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[ CAS No. 626-27-7 ] {[proInfo.proName]}

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Product Details of [ 626-27-7 ]

CAS No. :626-27-7 MDL No. :MFCD00009536
Formula : C14H26O3 Boiling Point : -
Linear Structure Formula :O(C(O)C6H13)2 InChI Key :DAPZDAPTZFJZTO-UHFFFAOYSA-N
M.W : 242.35 Pubchem ID :69376
Synonyms :

Calculated chemistry of [ 626-27-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 12
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 70.9
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.38
Log Po/w (XLOGP3) : 4.8
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 4.12
Consensus Log Po/w : 3.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.57
Solubility : 0.0645 mg/ml ; 0.000266 mol/l
Class : Soluble
Log S (Ali) : -5.44
Solubility : 0.000874 mg/ml ; 0.00000361 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.35
Solubility : 0.0109 mg/ml ; 0.000045 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 2.46

Safety of [ 626-27-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501 UN#:1760
Hazard Statements:H290-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 626-27-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 626-27-7 ]

[ 626-27-7 ] Synthesis Path-Downstream   1~97

  • 2
  • [ 626-27-7 ]
  • [ 375-85-9 ]
  • 3
  • [ 111-14-8 ]
  • [ 626-27-7 ]
YieldReaction ConditionsOperation in experiment
97% With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;
94% With magnesium basic carbonate; di-<i>tert</i>-butyl dicarbonate at 25℃; for 12h; 15 Examples 1420 In each example, methacrylic acid anhydride was produced under conditions the same as in Example 1 except that methacrylic acid was replaced with the type of carboxylic acid (6.0 mmol) shown in Table 1, and the amount of magnesium carbonate hydroxide relative to di-t-butyl dicarbonate was changed to 4 mol % or 8 mol %, while the rest of the conditions were set to be the same as in Example 1. The reaction results obtained 412 hours after the start of reactions are shown in Table 1.
With acetyl chloride
With acetic anhydride
With pyridine; thionyl chloride; diethyl ether at -10℃;
With methoxy acetylene
With dicyclohexyl-carbodiimide In dichloromethane
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 5 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0 - 20 °C
With acetic anhydride at 90 - 130℃; for 6h; For the production of the carboxylic acid anhydride of heptanoic acid (C7-acid), 860 g heptanoic acid are provided in a 2,000-ml-multi-neck flask with dephlegmator (partial condenser) and distillation bridge, and 445 g acetic anhydride are added at 90° C. under stirring. The reaction mixture is then refluxed at 130° C. for 6 h under stirring. The formed acetic acid and the excess acetic anhydride are then distilled off under vacuum. The heptanoic anhydride is obtained. Characterization is carried out by GC and GC-MS.

  • 4
  • [ 626-27-7 ]
  • [ 555-16-8 ]
  • 3<i>t</i>-(4-nitro-phenyl)-2-pentyl-acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium heptanoate at 140℃;
  • 5
  • [ 626-27-7 ]
  • [ 616-82-0 ]
  • [ 43049-38-3 ]
  • 6
  • [ 626-27-7 ]
  • [ 103846-35-1 ]
  • 2-n-hexyl-7-benzyl-5,6-dimethylpyrrolo<2,3-d>-1,3-oxazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With pyridine at 100℃; for 1.5h;
  • 7
  • [ 626-27-7 ]
  • [ 19083-21-7 ]
  • [ 123894-84-8 ]
YieldReaction ConditionsOperation in experiment
67.9% With trifluoroacetic acid In pyridine 1.) pyridine, 60 deg. C, 3h, 2.) CF3COOH, room temperatures, 2h;
  • 8
  • [ 626-27-7 ]
  • N-Phenyl-morpholine-4-carboxamidine [ No CAS ]
  • [ 148216-16-4 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In dichloromethane for 2.5h; Ambient temperature;
  • 9
  • [ 626-27-7 ]
  • C30H48N2O8 [ No CAS ]
  • Heptanoic acid {(5R,6S,7R)-7-[(2S,3S,6R,2'S,3'S,6'R)-6'-((5R,6S,7R)-4-heptanoylamino-6-methyl-2-oxo-1,8-dioxa-spiro[4.5]dec-7-yl)-3,3'-dimethyl-octahydro-[2,2']bipyranyl-6-yl]-6-methyl-2-oxo-1,8-dioxa-spiro[4.5]dec-4-yl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dmap
  • 10
  • [ 111-70-6 ]
  • [ 626-27-7 ]
YieldReaction ConditionsOperation in experiment
39% With oxygen In acetonitrile at 25℃; for 15h;
  • 11
  • [ 626-27-7 ]
  • [ 78-94-4 ]
  • [ 7018-92-0 ]
YieldReaction ConditionsOperation in experiment
55% With hydroxocobalamine hydrochloride; lithium perchlorate In N,N-dimethyl-formamide Ambient temperature; Irradiation; electrolysis at constant potential -0.95 V (vs. SCE);
  • 12
  • [ 626-27-7 ]
  • [ 122301-05-7 ]
  • 2,3,6,7-Tetrakis(heptanoyloxymethyl)tetrathiafulvalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 1-naphthalenesulfonic acid In dimethyl sulfoxide
  • 13
  • [ 626-27-7 ]
  • [ 1634-82-8 ]
  • 2-(4-Heptanoyloxy-phenylazo)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In chloroform at 25℃; for 24h;
  • 14
  • [ 626-27-7 ]
  • [ 172469-92-0 ]
  • 3-heptanamido-5-methyl-4-(3', 5'-dimethylphenyl)thio-pyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In toluene at 100℃; for 1.5h;
In diethyl ether; toluene 35 Preparation of 3-heptanamido-5-methyl-4-(3', 5'-dimethylphenyl)thio-pyridin-2(1H)-one (compound 11d) EXAMPLE 35 Preparation of 3-heptanamido-5-methyl-4-(3', 5'-dimethylphenyl)thio-pyridin-2(1H)-one (compound 11d) A solution of amine 8a (100 mg, 0.38 mmole) and heptanoic anhydride (0.14 g, 0.58 mmole) in toluene (4 ml) was heated at 100° C. for 1 hour 30 minutes. After evaporation of the toluene, 5 ml of diethyl ether was added. Once the precipitate had been obtained, the solvent was removed using a pipette. The solid was washed twice in this way with diethyl ether. After filtration, the residue was recrystallized in ethyl acetate. Product lld was obtained (17 mg, 50%) in the form of yellow micro-crystals: melting point 212-213° C.; NMR-1 H (DMSO-d6) δ 11.86 (1H, s, NH-1), 9.34 (1H, s, NH-3), 7.19 (1H, s, H-6), 6.86 (1H, s, H-4'), 6.76 (2H, s, H-2' and 6'), 2.28 (2H, t, J=7 Hz, COCH2), 2.22 (6H, s, CH3 -3' and 5'), 1.81 (3H, s, CH3 -5), 1.53 (2H, dd, J=7 Hz, COCH2 CH2), 1.28-1.21 (6H, m, (CH2)3), 0.86 (3H, t, J=6.5 Hz, (CH2)5 CH3). Anal. C21 H28 N2 O2 S (C, H, N, S).
  • 15
  • [ 626-27-7 ]
  • Acetic acid (3S,4R,4aR,6S,6aS,12R,12bS)-4-acetoxymethyl-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-3-yl ester [ No CAS ]
  • Heptanoic acid (3S,4R,4aR,6S,6aS,12R,12bS)-3-acetoxy-4-acetoxymethyl-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dmap; triethylamine In dichloromethane at 0 - 80℃;
  • 16
  • [ 626-27-7 ]
  • [ 71-43-2 ]
  • [ 1671-75-6 ]
YieldReaction ConditionsOperation in experiment
86% at 250℃; for 12h; other catalyst: HY-Zeolite;
  • 17
  • [ 626-27-7 ]
  • [ 210576-15-1 ]
  • Heptanoic acid 4,8a-dimethyl-3-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With dmap In dichloromethane
  • 18
  • [ 626-27-7 ]
  • [ 7689-03-4 ]
  • camptothecin-20-O-heptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With pyridine at 40℃; for 48h;
98% With pyridine 4 EXAMPLE 4 Camptothecin 20-O-heptanoate Using 15 ml heptanoic anhydrides, 13 ml pyridine, and 1.55 g starting camptothecin, the reaction was carried out in the same manner as in Example 1 whereby 2.0 g of the title compound was obtained as a gray-white powder, yield 98%, mp 270° C. (deformed at 210° C.). 1H NMR in CDCl3: 0.82 (3H, t, J=7.51 Hz, 28-methyl protons), 0.98 (3H, t, J=7.01 Hz, 19-methyl protons), 1.20-1.80 (8H, m, 24-, 25-, 26-, and 27-methylene protons), 2.10-2.30 (2H, m, 18-methylene protons), 2.40-2.60 (2H, m, 23-methylene protons), 5.29 (2H, s, 5-methyl protons), 5.38-5.72 (2H, dd, J=17.69, 17.22 Hz, 17-methylene protons), 7.23 (1H, s, 14-H), 7.68 (1H, t, J=7.30 Hz, 10-H), 7.84 (1H, t, J=7.42 Hz, 11-H), 7.95 (1H, d, J=8.60 Hz, 9-H), 8.22 (1H, d, J=8.32 Hz, 12-H), 8.40(1H, s, 7-H); 1H NMR in TFA: 0.74 (3H, s, 28-methyl protons), 0.99 (3H, s,19-methyl protons), 1.21 (6H, brs, 25-, 26-, and 27-methylene protons), 1.62 (2H, s, 24-methylene protons), 2.10-2.30 (4H, m, 18- and 23-methylene groups), 5.50-6.00 (4H, s+dd, s at 5.67 for 5-methylene protons, dd for 17-methylene protons), 7.80 (1H, s, 14-H), 7.99 (1H, s, 10-H), 8.23 (2H, s, 9-H and 11-H), 9.24 (1H, s, 7-H); 13C NMR(TFA): 8.63 (C19), 14.99 (C28), 24.66 (C27), 27.14 (C26), 31.07 (C24), 33.68 (C25), 34.29 (C18), 36.45 (C23), 54.34 (C5), 69.98 (C17), 79.50 (C20), 106.97, 114.39, 118.55, 127.11, 132.41, 133.79, 134.55, 140.46, 141.11, 142.00, 145.79, 148.14, 150.62, 153.00 (C2, C3, C6-C16, C16a), 180.57, 193.10 (C21, C22); mass m/e (relative intensity): 461 [(M+H)+, 100%], 331 [(M-C6H13COO), 20%], 317 [(M-C6H13COO-CH3+H), 10%], 303 [(M-C6H13COO-CO), 15%], 287 [(M-C6H13COO-CO2), 8%], 273 (2%), 261 (2%).
  • 19
  • [ 626-27-7 ]
  • [ 52485-79-7 ]
  • Buprenorphine enanthate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In N,N-dimethyl-formamide at 80℃; for 4h;
  • 20
  • [ 626-27-7 ]
  • [ 61-19-8 ]
  • adenosine-5'-phosphoric heptanoic anhydride [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With lithium hydroxide In tetrahydrofuran; pyridine; water at 40℃; for 0.166667h;
  • 21
  • [ 626-27-7 ]
  • [ 117173-75-8 ]
  • heptanoic acid 8-methoxy-1-methyl-1<i>H</i>-benzo[<i>de</i>][1,6]naphthyridin-9-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In pyridine at 20℃;
  • 22
  • [ 626-27-7 ]
  • [ 24704-84-5 ]
  • Heptanoic acid (6S,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With pyridine at 20℃; for 6h;
  • 23
  • [ 626-27-7 ]
  • [ 63-00-3 ]
  • Heptanoic acid (6R,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With pyridine at 20℃; for 6h;
  • 24
  • [ 626-27-7 ]
  • [ 25660-71-3 ]
  • 2-heptanoylamino-5-benzyl-mercapto-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With acetic acid at 35 - 40℃;
  • 25
  • [ 626-27-7 ]
  • [ 57260-73-8 ]
  • [ 688799-94-2 ]
YieldReaction ConditionsOperation in experiment
67% In N,N-dimethyl-formamide at 20℃; for 2h;
67% In N,N-dimethyl-formamide at 20℃; for 2h; 5 A solution of di-t-butyl dicarbonate (0.50 g, 2.29 mmol) in dioxane (20 mL) was added over a period of 1 hr to a solution of 1,2-diaminoethane (1.10 g, 18.3 mmol) in dioxane (20 mL). The mixture was allowed to stir for 22 hr and the solvent was evaporated to dryness. Water (30 mL) was added to the residue and the insoluble bis-substituted product was removed by filtration. The filtrate was extracted with methylene chloride (3 X 30 mL) and the methylene chloride evaporated to yield ix as an oil (0.35 g, 95%).[0162] A solution of heptanoic anhydride (0.91 g, 3.75 mmol; chloroformic acid pentyl ester for 777 and pentyl isocyanate for 766) and ix (0.50 g, 3.13 mmol) in DMF (20 mL) was stirred for 2 hr at room temperature. Then the solvent was evaporated. The residue was partitioned between ether (30 mL) and water (30 mL). The ether layer was dried over Na2SO4 and evaporated. The residue was purified by using column chromatography on silica gel eluting hexane and ethyl acetate (1:1) to get 0.57 g (67%) of alkylated N-t- butoxycarbonyl amine (x).[0163] To a solution of x in dioxane (10 mL) was treated with 4M hydrochloric acid (2mL) in dioxane, and the mixture was stirred for lhr at room temperature. Then the solvent was evaporated to dryness, and the residual solid was dissolved in DMF (10 mL) and treated with TEA (0.58 mL, 4.19 mmol) and 3-chlorophenyl isocyanate (0.32 g, 2.10 mmol) at room temperature. After stirring for 5 hr, the product was extracted with ether (30 mL), and the ether was washed with water (30 mL), dried over Na2SO4, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (1:1) to afford 0.68 g (100%) of 765. 5(CDCl3): 0.84 (t, 3H, J= 6.9 Hz), 1.16-1.25 (6H, m), 1.55-5.61 (2H, m), 2.21-2.24 (2H, m), 3.31-3.40 (4H, m), 6.27 (IH, s), 6.90-6.95 (2H, m), 7.18-7.20 (2H, m), 7.56 (IH, s), 8.07 (IH, s), [M + H]+ 326.25
  • 26
  • [ 626-27-7 ]
  • [ 4459-90-9 ]
  • 1-(3-chlorophenyl)-3-(2-hexylcarbonyloxyethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;
70% With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; 4 To a solution of 2-aminoethanol (2.98 g, 48.8 mmol) in DMF (30 mL) was added 3- chlorophenol isocyanate (2.50 g, 16.3 mmol) at O0C. The reaction mixture was stirred for 5 hr at room temperature. The solvent was evaporated, and the residue was partitioned between ether (30 mL) and IN hydrochloric acid (20 mL), and the ether layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (1:1) to provide 1.49 g (40%) of urea alcohol (viii) as a white solid.[0157] To a solution of viii (1.0Og, 4.60 mmol) and TEA (0.97 mL, 6.90 mmol) in DMF (15 mL) was added a solution of heptanoic anhydride (2.23 g, 9.20 mmol) in DMF (5 mL) at room temperature. The reaction was stirred for 12 hr, and the solvent was evaporated. The residue was partitioned between ether (30 mL) and cold IN hydrochloric acid (20 mL). The ether layer was washed with brine, dried over Na2SO4, and evaporated. The residual solid was purified using silica gel column chromatography (hexane : ethyl acetate = 3 : 1) to afford 1.05 g (70%) of 761. δ(CDCl3): 0.87 (t, 3H, J= 6.9 Hz), 1.20-1.29 (6H, m), 1.60-1.62 (2H, m), 2.22-2.29 (2H, m), 3.50-3.55 (2H, m), 4.09-4.20 (2H, m), 5.32 (IH, s), 7.01-7.06 (2H, m), 7.16-7.22 (2H, m), 7.40 (IH, s), [M + H]+ 327.15
  • 28
  • [ 626-27-7 ]
  • [ 619-56-7 ]
  • [ 39549-66-1 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid at 100℃; for 0.05h; Microwave irradiation; 4.2. Typical procedure for the synthesis of N-acylation of amide derivatives General procedure: Amide derivatives (1.0 mmol), acid anhydrides (3.0 mmol), and 2 drops of concd H2SO4 were placed in a 50 mL round bottom flask equipped with a reflux condenser. The reaction flask was microwave irradiated (50 W, 100 °C) for 3 min with stirring. After the reaction, the solution was extracted with ethyl acetate (2×10 mL), and the combined organic layer was washed with 5% aq NaHCO3 (2×10 mL), and brine (20 mL), dried over anhydrous MgSO4, and evaporated to provide the crude material. The crude material was purified by flash column chromatography using various hexane/ethyl acetate eluent systems to afford the desired products 1a-22a.
40% With sulfuric acid In toluene for 1h; Heating;
  • 29
  • [ 626-27-7 ]
  • [ 6631-53-4 ]
  • 2-phenyl-4-(D-erithro-3'-heptanoyloxy-1',2'-dihydroxypropyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With Candida antarctica lipase B In di-isopropyl ether at 42 - 45℃; for 9h;
  • 30
  • [ 626-27-7 ]
  • [ 15476-33-2 ]
  • 2-phenyl-4-(D-threo-3'-heptanoyloxy-1',2'-dihydroxypropyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With Candida antarctica lipase B In di-isopropyl ether at 42 - 45℃; for 1h;
  • 31
  • [ 626-27-7 ]
  • [ 6341-06-6 ]
  • 2-phenyl-4-(D-arabino-4'-heptanoyloxy-1',2',3'-trihydroxybutyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With Candida antarctica lipase B In di-isopropyl ether at 42 - 45℃; for 8h;
  • 32
  • [ 626-27-7 ]
  • [ 15476-32-1 ]
  • 2-phenyl-4-(D-lyxo-4'-heptanoyloxy-1',2',3'-trihydroxybutyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With Candida antarctica lipase B In di-isopropyl ether at 42 - 45℃; for 14h;
  • 33
  • [ 355388-24-8 ]
  • [ 626-27-7 ]
  • (S)-2-Heptanoylamino-3-[(R)-1-(3-piperidin-4-yl-propionyl)-piperidine-3-carbonyl]-amino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: (2S)-2-amino-3-[((3R)-1-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]propanoyl}-3-piperidinyl)carbonyl]amino}propanoic acid; n-heptanoic anhydride With sodium hydroxide In tetrahydrofuran at 20℃; for 1h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 2h;
  • 34
  • [ 626-27-7 ]
  • [ 145325-89-9 ]
  • heptanoic acid (7-heptanoylamino-[1,8]naphthyridin-2-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With pyridine; dmap at 100℃; for 48h;
  • 35
  • [ 626-27-7 ]
  • [ 145918-75-8 ]
  • (-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolane-4-yl]-4-N-heptanoyl-cytosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In methanol at 55℃; for 6h;
  • 36
  • [ 626-27-7 ]
  • corosolic acid [ No CAS ]
  • C37H60O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With pyridine at 20℃;
  • 37
  • [ 626-27-7 ]
  • 1,5-bis-(4-chloro-phenyl)-3-hexyl-1<i>H</i>-[1,2,4]triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 40 percent / H2SO4 / toluene / 1 h / Heating 2: 12 percent / NaOAc / acetic acid / 22 h / Heating
  • 38
  • [ 626-27-7 ]
  • LH-21 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 40 percent / H2SO4 / toluene / 1 h / Heating 2: 9 percent / NaOAc / acetic acid / 22 h / Heating
  • 39
  • [ 626-27-7 ]
  • 1,5-bis-(2,4-dichloro-phenyl)-3-hexyl-1<i>H</i>-[1,2,4]triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / H2SO4 / toluene / 1 h / Heating 2: 6 percent / NaOAc / acetic acid / 22 h / Heating
  • 40
  • [ 626-27-7 ]
  • [ 134461-75-9 ]
  • [ 21043-29-8 ]
YieldReaction ConditionsOperation in experiment
70% In 1-methyl-1H-imidazole at 130℃; for 0.5h; [0031] 6-Heptanoylamido purine (1): [0032] Adenine (40.0g; 296.3 mmol) was suspended in N-methylimidazole (100-ml). To the mechanically stirred mixture under nitrogen atmosphere was added heptanoic anhydride (125 ml; 476.2 mmol) and the mixture was heated at 130 C. to obtain a clear solution. The solution was warmed at 130 C. for 30 minutes and was cooled to 90 C. with stirring. To the stirred solution at 90 C. was added methanol (700 ml) slowly and the mixture was stirred at 40 C. for 5 minutes. The separated solid was collected by filtration and dried at 80 C./0.3 mm Hg/3 h to obtain crude product. This material was crystallized from boiling ethanol (700 ml) to obtain title 1, 51.0 g (70%); m.p. 189-190 C. 1H NMR (DMSO-d6): ? 12.30 and 11.87 (brS, 1H, each, D2O exchangeable, NH), 8.67 (S, 1H, C2H), 8.46 (S, 1H, C8H), 2.56 (t, 2H,CH2), 1.66 (m, 2H), 1.31 (m, 6H), 0.87 (t, 3H, CH3) Analysis calculated for C12H17N5O (247.24): C, 58.28; H, 6.93; N, 28.32. Found: C, 58.21; H, 7.05 N, 28.61.
  • 41
  • [ 626-27-7 ]
  • [ 1839-18-5 ]
  • [ 662118-71-0 ]
YieldReaction ConditionsOperation in experiment
72% at 130 - 210℃; 9 [0033] 2-Chloro-6-heptanoylamido purine (2) [0034] 2-Chloroadenine (10.0 g; 59 mmol) was heated with N-methylimidazole (25 ml) and heptanoic anhydride (30 ml; 114.2 mmol) at 130 C. the same way as described for 6-heptanoylamido purine to obtain the 2-chloro-6-heptanoylamido purine 2, 12.0 g (72%); m.p. 269-270 C. 1H NMR (DMSO-d6): ? 12.32 and 11.47 (br s, 1H each, D2O exchangeable; NH), 8.41 (s, 1H, C8H), 2.51 (t, 2H, CH2), 1.59 (m, 2H, CH2), 1.25 (m, 6H, CH2), 0.83 (t, 3H,CH3), Analysis calculated for C12H16ClN5O (281.74): C, 51.15; H, 5.72; N, 24.85; Cl, 12.58 Found: C, 51.12; H, 5.76; N, 24.91; Cl, 12.46. [0066] 2-Chloro-6-heptanoylamidopurine(2) [0067] 6-Amino-2-chloropurine (2.37 g, 14 mmol) was suspended in dry xylene (5 mL), and heptanoic anhydride (4.0 mL, 15.26 mmol) was added to the suspension under nitrogen atmosphere with magnetic stirring. The mixture was warmed at reflux temperature for 2 h and concentrated in vacuo (high vacuum, 60 C. water bath) to a semisolid mass. Fresh heptanoic anhydride (4.0 mL, 15.26 mmol) was added to the residue and the mixture was heated with stirring in an oil bath (210 C.). At this point, a clear orange solution was observed (internal temperature 205-207 C.). The clear solution was rapidly cooled in an ice-bath (2-5 C.) with magnetic stirring. Methanol (30 mL) was added to the mixture (internal temperature 55 C.) and stirring (ice-bath) was continued for an additional 30 min. A solid separated that was collected by filtration, washed with methanol (1?10 mL) followed with diethyl ether (2?20 mL) . The solid was dried at 70 C./0.3 mm Hg for 3 h to give 3.01 g (76%) of 2 as off-white solid, mp 269-270 C. Rf0.82 (20% methanol-methylene chloride). 1H NMR (DMSO-d6): ? 12.32 (s, 1 H, D2O-exchangeable, NH), 11.47 (s, 1 H, D2O-exchangeable, NH), 8.413 (s, 1H, C8H), 2.51 (t, 2H, CH2), 1.60 (m, 2 H, CH2), 1.254 (m, 6H, CH2), 0.83 (6, 3 H, CH3).
  • 42
  • [ 577774-39-1 ]
  • [ 626-27-7 ]
  • 1-[(3S)-dimethylaminopyrrolidin-1-yl]-2-(2-hetanoyloxyethyl)-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With pyridine at 20℃; for 18h; 71 Example 71; 1-[(3S)-dimethylaminopyrrolidin-1-yl]-2-(2-hetanoyloxyethyl)-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile (#71) 108 µl (413 µmol) of heptanoic anhydride was added to a mixture of 100 mg (275 µmol) of 1-[(3S)-dimethylaminopyrrolidin-1-yl]-2-(2-hydroxyethyl)-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile (No.66) and 534 µl (6.60 mmol) of pyridine at room temperature, and stirred for 18 hours. The solvent was evaporated under reducedpressure, and the residue was dissolved in 20 ml of ethyl acetate. The solution was washed with 10 ml of aqueous saturated sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was applied to a silica gel column chromatography. This was eluted with a mixed solvent of dichloromethane/methanol (30/1, v/v) to obtain a crude product of the entitled compound. This was recrystallized from ethyl acetate/n-hexane to obtain 69 mg (53 %) of the entitled compound (No.71) as a yellow crystal. MS(EI)m/z:476(M+).1H-NMR(400MHz, CDCl3)δ: 0.83-0.92(3H, m), 1.28(6H, brs), 1.51-1.68(2H, m), 2.15-2.50(5H, m) , 2.36(6H, s), 2.77(3H, s), 3.07(3H, brs), 3.25-3.80 (3H, m), 4.21-4.33(2H, m) , 7.33-7.41(1H, m), 7.50-7.59(1H, m), 7.97-8.15(1H, m), 8.00(1H, d, J=8.07Hz). IR(ATR): 2224, 1728, 1624, 1589, 1475, 1446, 1306, 1169 cm-1.
  • 43
  • triethoxysilylpropylmercaptan [ No CAS ]
  • [ 626-27-7 ]
  • 3-heptanoyl-1-thiopropyltriethoxysilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.7% With tri-n-propylamine In Petroleum ether at 20 - 60℃; for 7h; 13 Example 13: TNPA assisted reaction of heptanoic anhydride with MPTES with water/brine wash [0079] At ambient temperature, 250.3 g MPTES (1.05 moles), 157.3 g TNPA (1. 10 moles) and 300 g VM&P naphtha were added to 2-L 4-neck round bottom flask with bottom take-off equipped with mechanical stirrer, dry ice condenser, N2 inlet & thermocouple, and additional funnel. MPTES, the amine, and the solvent were mixed and 242.4 g (1.00 moles) of heptanoic anhydride were added slowly through the addition funnel. The addition was completed during a one-hour period. During the addition, the exotherm was only 4°C. The mixture was heated to 60°C and held at that temperature for 6 hours. The slurry was cooled to 35 °C and then water washed with 204 g 10% NaCl solution (5 min. stirring, 15 min. settling). The organic layer was colorless and the aqueous layer was white opaque. The organic phase was dried with 5 g of anhydrous magnesium sulfate, filtered, and vacuum stripped at 30 mm Hg. The temperature was increased slowly to 130 °C and held for 30 minutes. The product was polish filtered through a 1-micron filter pad. The product weighed 308.9 g and contained 33.7% of the pure triethoxy-ester, 3-HEPTANOYL-1-THIOPROPYLTRIETHOXYSILANE, as well as 2.2% MPTES, and 57% eluted heavies.
  • 44
  • 8a-[[[6-(hydroxy)tetrahydro-7-hydroxy-2,5-methanofuro[2,3-d]-1,3-dioxol-2-yl]oxy]methyl]-4-formyl-4,4a,5,6,7,7a,8,8a-octahydro-7-methyl-3-(1-methylethyl)-1,4-methano-s-indacene-3a(1H)-carboxylic acid [ No CAS ]
  • [ 626-27-7 ]
  • 8a-[[[6-(n-heptanoyloxy)tetrahydro-7-hydroxy-2,5-methanofuro[2,3-d]-1,3-dioxol-2-yl]oxy]methyl]-4-formyl-4,4a,5,6,7,7a,8,8a-octahydro-7-methyl-3-(1-methylethyl)-1,4-methano-s-indacene-3a(1H)-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine 9 Preparation of 8a-[[[6-(n-heptanoyloxy)tetrahydro-7-hydroxy-2,5-methanofuro[2,3-d]-1,3-dioxol-2-yl]oxy]methyl]-4-formyl-4,4a,5,6,7,7a,8,8a-octahydro-7-methyl-3-(1-methylethyl)-1,4-methano-s-indacene-3a(1H)-carboxylic acid (14) EXAMPLE 9 Preparation of 8a-[[[6-(n-heptanoyloxy)tetrahydro-7-hydroxy-2,5-methanofuro[2,3-d]-1,3-dioxol-2-yl]oxy]methyl]-4-formyl-4,4a,5,6,7,7a,8,8a-octahydro-7-methyl-3-(1-methylethyl)-1,4-methano-s-indacene-3a(1H)-carboxylic acid (14) 30 mg of compound (2) was dissolved in 1.0 ml of pyridine and stirred together with 54.7 μl of n-heptanoic anhydride at room temperature. After 42 hours, 29.6 μl of n-heptanoic anhydride was added, and the reaction was conducted for another 7 hours. The reaction solution was concentrated in vacuo, charged onto a silica gel column (Kieselgel 60, Merck, 1.5φ*30 cm) and eluted with chloroform-methanol (100:1). The fraction containing the desired product was concentrated in vacuo to give the desired compound as a crude product. For further purification, it was subjected to Sephadex LH-20 column chromatography (Pharmacia, 1.5φ*90 cm) and eluted with methanol. The fraction containing the desired product was concentrated in vacuo to dryness to give 12.1 mg of compound (14). Rf: 0.66 (Kieselgel 60F254, Merck, chloroform-methanol; 10:1). FAB-MS(m/z): 603[M+H]+. 1 H-NMR(δ ppm, 500 MHz, CDCl3),:9.70(1H, s), 6.09 (1H, brd, J=3.7 Hz), 5.74(1H, brd, J=4.0 Hz), 4.75(1H, m), 4.70(1H, t, J=3.7 Hz), 4.39(1H, m), 3.99(1H, d, J=9.8 Hz), 3.96(1H, d, J=9.8 Hz), 3.68(1H, d, J=1.5 Hz), 2.80(1H, t, J=3.7 Hz), 2.41(2H, m), 2.32(1H, m), 1.82-2.10(6H, m), 1.74(2H, m), 1.64(2H, m), 1.20-1.40 (8H, m), 1.02(3H, d, J=6.7 Hz), 1.00(1H, m), 0.95(3H, d, J=6.7 Hz), 0.90(3H, t, J=7.3 Hz), 0.79(3H, d, J=6.7 Hz).
  • 45
  • [ 39209-98-8 ]
  • [ 626-27-7 ]
  • [ 144-55-8 ]
  • 2-(2-heptanoyloxybenzoyl)-3,4,5-tribromopyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform; water 2 EXAMPLE 2 EXAMPLE 2 Dissolved in 5 ml of pyridine was 0.63 g of 2-(2-hydroxybenzoyl)-3,4,5-tribromopyrrole, followed by the addition of 1.5 ml of enanthic anhydride. The resultant mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into 20 ml of ice water, followed by extraction with ether. The extract was washed successively with 1 N hydrochloric acid, a 2% aqueous solution of sodium hydrogen-carbonate, and water. The solution thus washed was dried over anhydrous sodium sulfate and then dried to solid under reduced pressure. The residue was subjected to chromatography on a silica gel column, and from chloroform elude fractions, 0.25 g of 2-(2-heptanoyloxybenzoyl)-3,4,5-tribromopyrrole (Compound No. 3) was obtained.
  • 46
  • [ 626-27-7 ]
  • [ 79243-67-7 ]
  • 17β-heptanoyloxy-1α-methyl-17α-n-propyl-5α-androstan-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In pyridine 11 EXAMPLE 11 EXAMPLE 11 400 mg of 17β-hydroxy-1α-methyl-17α-n-propyl-5α-androstan-3-one is stirred for 42 hours at room temperature in 1.6 ml of pyridine and 0.8 ml of enanthic anhydride with the addition of 40 mg of 4-dimethylaminopyridine. The mixture is diluted with ether, washed with water, dried, and evaporated. The residue is chromatographed on silica gel, yielding 370 mg of 17β-heptanoyloxy-1α-methyl-17α-n-propyl-5α-androstan-3-one as an oil.
  • 47
  • [ 79800-97-8 ]
  • [ 626-27-7 ]
  • 17α-ethynyl-17β-heptanoyloxy-18-methyl-4,15-estradiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In pyridine 6 17α-Ethynyl-17β-heptanoyloxy-18-methyl-4,15-estradiene EXAMPLE 6 17α-Ethynyl-17β-heptanoyloxy-18-methyl-4,15-estradiene 300 mg of 17α-ethynyl-18-methyl-4,15-estradien-17β-ol in 4 ml of pyridine is stirred at room temperature with 2 ml of enanthic anhydride and 60 mg of 4-dimethylaminopyridine for 18 hours. The mixture is poured into ice/water, extracted with ethyl acetate, and the solution washed with water. After chromatography of the crude product on silica gel with ethyl acetate/hexane, 190 mg of 17α-ethynyl-17β-heptanoyloxy-18-methyl-4,15-estradiene is obtained as an oil.
  • 48
  • 17α-chloroethynyl-13β-ethylgon-4-en17β-ol [ No CAS ]
  • [ 626-27-7 ]
  • [ 2528-61-2 ]
  • 17α-chloroethynyl-3,17-diheptanoyloxy-13β-ethylgona-3,5-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In methanol 268 17α-Chloroethynyl-3,17β-diheptanoyloxy-13β-ethylgona-3,5-diene EXAMPLE 268 17α-Chloroethynyl-3,17β-diheptanoyloxy-13β-ethylgona-3,5-diene Heat a mixture of 17α-chloroethynyl-13β-ethylgon-4-en17β-ol (3 g.), n-heptanoic anhydride (50 cc.), pyridine (2.4 cc.) and n-heptanoyl chloride (25 cc.) at 100° for 3-1/2 hours. Filter the cooled solution and distil off the remaining acylating agent and pyridine at 0.5 mm. to give the title compound (3.7 g). Recrystallise from methanol to obtain a waxy solid m.p. 56°-65°, infrared absorption peaks at 3.99, 6.5, 5.75 μ.
  • 49
  • 17α-chloroethynyl-13β-ethylgon-4-ene-3β,17β-diol [ No CAS ]
  • [ 626-27-7 ]
  • 17α-Chloroethynyl-13β-ethyl-3β-heptanoyloxygon-4-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; methanol 264 17α-Chloroethynyl-13β-ethyl-3β-heptanoyloxygon-4-ene EXAMPLE 264 17α-Chloroethynyl-13β-ethyl-3β-heptanoyloxygon-4-ene Dissolve 17α-chloroethynyl-13β-ethylgon-4-ene-3β,17β-diol (1 g.) in pyridine (1 cc.) and n-heptanoic anhydride (1.1 cc.), allow the mixture to stand for 24 hours, pour into water and stir for 2 hours. Acidify the mixture with dilute sulphuric acid and stir for a further 2 hours. Isolate the product with ether and recrystallise from methanol to obtain the title product (0.65 g.), m.p. 142°-144°.
  • 50
  • [ 626-27-7 ]
  • [ 3641-08-5 ]
  • Heptanoyl-s-triazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In diethyl ether; acetonitrile 3 Preparation of 1(and 2 and 4)-Heptanoyl-s-triazole-3-carboxamide EXAMPLE 3 Preparation of 1(and 2 and 4)-Heptanoyl-s-triazole-3-carboxamide To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 4 g. of heptanoic anhydride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 17.5 hours. The heterogeneous mixture is filtered, washed with diethyl ether, cold water and then diethyl ether, dried for about 15 minutes and then dried in vacuo yielding 4 g. of colorless solid. The solid is extracted in hot dry acetonitrile and on cooling to room temperature the product is collected, washed with acetonitrile and dried in vacuo, yielding 0.4 g. of colorless crystals, m.p. 184°-187° C. (dec.).
  • 51
  • [ 66853-15-4 ]
  • [ 626-27-7 ]
  • [ 66853-22-3 ]
YieldReaction ConditionsOperation in experiment
In pyridine 25 EXAMPLE 25 EXAMPLE 25 1.5 g. of crude 11β,21-dihydroxy-17α-propionyloxy-1,4,8-pregnatriene-3,20-dione in 15 ml. of pyridine and 10 ml. of enanthic anhydride is agitated overnight at room temperature. The mixture is worked up as usual, and the excess enanthic acid is removed by steam distillation. The crude product is chromatographed on 300 g. of silica gel with a methylene chloride-acetone gradient (0-12% acetone), thus isolating 680 mg. of 21-heptanoyloxy-11β-hydroxy-17α-propionyloxy-1,4,8-pregnatriene-3,20-dione.
  • 52
  • [ 102-54-5 ]
  • [ 626-27-7 ]
  • [ 68209-43-8 ]
YieldReaction ConditionsOperation in experiment
63% With boron trifluoride diethyl etherate In dichloromethane ferrocene and 2 equivs. of acid anhydride suspended in CH2Cl2 and cooledto 0°C, boron trifluoride etherate added over 10 min, stirred at room temp. for 3 h; poured into ice H2O, sepd., the org. layer washed (satd. NaHCO3 soln.), dried (MgSO4), solvent-removed, flash-chromd. (SiO2, cyclohexane/EtOAc);obtained as oil;
  • 53
  • [ 85-44-9 ]
  • [ 88-69-7 ]
  • [ 626-27-7 ]
  • [ 95-48-7 ]
  • [ 1031825-08-7 ]
  • [ 1031825-20-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: phthalic anhydride; 2-(1-methylethyl)phenol; ortho-cresol With methanesulfonic acid at 100 - 105℃; for 20h; Stage #2: With sodium hydroxide In water at 0 - 60℃; Stage #3: n-heptanoic anhydride In water at 50 - 90℃; 1 100 grams of phthalic anhydride, 110 grams of methanesulfonic acid, and 98.8 grams of o-cresol and 41.5 grams of o-iso-propylphenol were stirred and heated to 100-105° C. for 20 hours. The reaction mixture is then drowned and the pH of the reaction mixture is adjusted to 9-10 by addition of 25% sodium hydroxide while maintaining a temperature below 60° C. Aromatic 200, 300 grams, is now added to the aqueous suspension of the mixture of phthaleins. The reaction mixture is made highly alkaline by addition of 225 grams of 25% sodium hydroxide and then esterified by slow addition of 342 grams n-heptanoic anhydride while maintaining a temperature below 50° C. and a pH of 10 or higher. When esterification is complete, the reaction mixture is then heated to 90° C. and transferred to a separatory funnel where the layers are allowed to separate. The lower aqueous phase is removed and discarded while the upper organic phase containing the mixture of esterified phthaleins is dried free of water by heating it under vacuum to a temperature of 120° C. The dried product is further diluted with Aromatic 200 to a weight of 1000 grams. The product is then filtered to remove any suspended insoluble material.
  • 54
  • [ 85-44-9 ]
  • [ 89-72-5 ]
  • [ 626-27-7 ]
  • [ 2051-49-2 ]
  • [ 95-48-7 ]
  • [ 1031825-13-4 ]
  • [ 1031825-08-7 ]
  • [ 1031825-14-5 ]
  • [ 1031825-09-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: phthalic anhydride; 2-sec-butylphenol; ortho-cresol With methanesulfonic acid at 100 - 105℃; for 20h; Stage #2: With sodium hydroxide In water at 0 - 60℃; Stage #3: n-heptanoic anhydride; n-hexanoic anhydride In water at 50 - 90℃; 5 100 grams of phthalic anhydride, 110 grams of methanesulfonic acid, and 98.8 grams of o-cresol and 45.8 grams of o-sec-butylphenol were stirred and heated to 100-105° C. for 20 hours. The reaction mixture is then drowned and the pH of the reaction mixture is adjusted to 9-10 by addition of 25% sodium hydroxide while maintaining a temperature below 60° C. Aromatic 200, 300 grams, is now added to the aqueous suspension of the mixture of phthaleins. The reaction mixture is made highly alkaline by addition of 225 grams of 25% sodium hydroxide and then esterified by slow addition of a mixture of 171 grams n-heptanoic anhydride and 160.5 grams of hexanoic anhydride while maintaining a temperature below 50° C. and a pH of 10 or higher. When esterification is complete, the reaction mixture is then heated to 90° C. and transferred to a separatory funnel where the layers are allowed to separate. The lower aqueous phase is removed and discarded while the upper organic phase containing the mixture of esterified phthaleins is dried free of water by heating it under vacuum to a temperature of 120° C. The dried product is further diluted with Aromatic 200 to a weight of 1000 grams. The product is then filtered to remove any suspended insoluble material.
  • 55
  • [ 85-44-9 ]
  • [ 89-72-5 ]
  • [ 626-27-7 ]
  • [ 95-48-7 ]
  • [ 1031825-08-7 ]
  • [ 1031825-09-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: phthalic anhydride; 2-sec-butylphenol; ortho-cresol With methanesulfonic acid at 100 - 105℃; for 20h; Stage #2: With sodium hydroxide In water at 0 - 60℃; Stage #3: n-heptanoic anhydride In water at 50 - 90℃; 1 A 2 liter flask fitted with stirrer, thermometer and heating mantel is charged with 100 grams of phthalic anhydride, 110 grams of methanesulfonic acid, and 98.8 grams of o-cresol and 45.8 grams of o-sec-butylphenol. The mixture is stirred and heated to 100-105° C. for 20 hours. The reaction mixture is then drowned into 800 grams of ice and water mixture. The pH of the reaction mixture is then adjusted to 9-10 by addition of 25% sodium hydroxide while maintaining a temperature below 60° C. Aromatic 200, 300 grams, is now added to the aqueous suspension of the mixture of phthaleins. The reaction mixture is made highly alkaline by addition of 225 grams of 25% sodium hydroxide and then esterified by slow addition of 342 grams n-heptanoic anhydride maintaining a temperature below 50° C. and a pH of 10 or higher. The reaction mixture is then stirred till esterification is complete, as determined by thin layer chromatography. The reaction mixture is then heated to 90° C. and transferred to a separatory funnel where the layers are allowed to separate. The lower aqueous phase is removed and discarded while the upper organic phase containing the mixture of esterified phthaleins is dried free of water by heating it under vacuum to a temperature of 120° C. The dried product is further diluted with Aromatic 200 to a weight of 1000 grams. The product is then filtered to remove any suspended insoluble material
  • 56
  • [ 626-27-7 ]
  • [ 1003193-29-0 ]
  • [ 1003193-43-8 ]
YieldReaction ConditionsOperation in experiment
33% In 1,4-dioxane; water at 100℃; for 24h; 15 Compound 1 (1.27 g, 3.3 mmol) and heptanoic acid anhydride (1.8 mL, 6.8 mmol) were added to a solvent mixture of dioxane (14 mL) and water (5 mL), and the mixture was stirred for one day at 100°C. After completion of reaction, the reaction mixture was extracted with ethyl acetate (50 mL), and the organic layer was neutralized with 1N aqueous sodium hydroxide. The resultant mixture was washed with saturated brine (50 mL) and then dried over magnesium sulfate. Magnesium sulfate was removed through filtration, and the solvent was evaporated under reduced pressure. The residue was purified through silica gel chromatography (4% methanol/chloroform solvent mixture). The eluate was concentrated, and the residue was recrystallized from isopropanol/hexane, to thereby yield Compound 15 (0.55 g, 33%).
  • 58
  • [ 626-27-7 ]
  • [ 1346530-82-2 ]
  • [ 1346530-87-7 ]
YieldReaction ConditionsOperation in experiment
87.2% With pyridine at 0 - 20℃;
  • 61
  • [ 626-27-7 ]
  • [ 85721-33-1 ]
  • [ 1186385-02-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ciprofloxacin With triethylamine In dichloromethane at 0℃; for 0.25h; Stage #2: n-heptanoic anhydride In dichloromethane at 0 - 20℃; General methods for the synthesis of N-acyl ciprofloxacins 2a-r General procedure: Method B: Ciprofloxacin (500 mg, 1.5 mmol) and triethylamine (300 μL, 2 mmol) were stirred in 20 mL of methylene chloride at 0 °C for 15 min. The desired acid anhydride (3 mmol) was added dropwise. The suspension was allowed to stir at room temperature until a clear solution was observed. To this solution, hexane was added drop wise until a white precipitate formed. The precipitate was then filtered off and dried. If further purification was needed, the desired compound was isolated via flash chromatography using 20% methanol in dichloromethane as the eluent.
  • 62
  • [ 626-27-7 ]
  • [ 317842-50-5 ]
  • C26H39NO6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In dichloromethane at 80℃; for 24h; Inert atmosphere;
  • 63
  • [ 856409-63-7 ]
  • [ 626-27-7 ]
  • 6,8-dioxo-7-phenyl-2-tosyl-1,2,3,5,5a,6,7,8,8a,8b-decahydropyrrolo[3,4-e]isoindol-4-yl heptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: N-(but-2-ynyl)-4-methyl-N-(2-oxoethyl)-benzenesulfonamide; n-heptanoic anhydride With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; hydrogen In dichloromethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: In dichloromethane at 80℃; for 16h; Schlenk technique; Inert atmosphere;
  • 64
  • [ 626-27-7 ]
  • 1-acetoxy-6α-hydroxy-4αH-1,10-secoeudesma-5(10),11(13)-dien-12,8β-olide [ No CAS ]
  • [ 1613152-31-0 ]
YieldReaction ConditionsOperation in experiment
85% With dmap; triethylamine In dichloromethane at 0 - 20℃; 4.1.4.1. Procedure for the synthesis of ABL analogues (1-11). General procedure: To a suspension of acid anhydride (0.15 mmol) and DMAP in anhydrous CH2Cl2 (1 mL) in an ice-bath was added ABL (0.1 mmol) in anhydrous CH2Cl2 (1 mL) solution. After completion of the reaction from 10 min to 4 h at room temperature, ice water (2 mL) was added to the solvent and stirred for 20 min, then extracted with CH2Cl2, dried and filtered. After removal of the solvent, the crude product was purified by silica gel chromatography (EtOAc/PE) to afford compounds 1-11 in 85%-98% yields.
  • 65
  • [ 626-27-7 ]
  • [ 96551-22-3 ]
  • 3-heptanoyloxymethylindole-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 6: 3-Heptanoyloxymethyl-indole-1 -carboxylic acid tert-butyl ester [CPL- 2012-159] Charged 3-hydroxymethylindole-1 -carboxylic acid tert-butyl ester is added in to a flask and added Dimethyl aminopyridine, Triethyl amine and THF at 0C. Maintained the reaction for 10 Minutes and then added Heptanoic anhydride drop wise slowly at 0C and maintained the reaction for 3 hours. After completion of the reaction added citric acid solution to the reaction mixture and stirred well. Extract the reaction mass with ethyl acetate twice. Dried the organic layer over sodium sulfate and concentrated the organic layer at 40C. Thus obtained residue is chromatographed on silica gel using Hexane as the eluent.
  • 66
  • [ 626-27-7 ]
  • C6H16Cl2N2O2Pt [ No CAS ]
  • cis-bis(heptanoato)amine(cyclohexylamine)dichloridoplatinum(IV) cisplatin [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.8% In acetonitrile for 15h; Reflux; 2.5. Synthesis of cis, trans, cis-[PtCl2(OH)2achNH3] (4) and then cis,trans, cis-[PtCl2(OC(O)(CH2)5CH3)2achNH3] (5) A suspension of complex 3 (0.141 g, 0.37 mmol) in 1.40 mL of H2O was stirred at r.t. for 3 h. The suspension was heated to70 °C before 365 lL of H2O2 (30%) was added and stirred for 2 h.The reaction mixture was then cooled at r.t. and let stand overnight before it was cooled in an ice bath for 0.5 h. The precipitate was collected via vacuum filtration. The product was washed with1.5 mL of H2O, ethanol and then diethyl ether. A very pale yellow/off-white powder obtained: 85.7 mg (55.8% yield). Complex 5 was then prepared in a similar manner as [Pt(cis-1,4-dach)-trans-(acetate)2Cl2] [28,29]. To a suspension of 4 (75 mg,0.18 mmol) in 15 mL acetonitrile was added heptanoic anhydride(0.714 mL, 15-fold). The reaction mixture was refluxed for 15 hand the clear yellow solution obtained was evaporated to dryness under reduced pressure. The resulting yellow residue was redissolved in approximately 3 mL of acetone and centrifuged. The supernatant was saved and evaporated to a minimum volumeand kept in the refrigerator (7 °C). The pale yellow precipitateobtained was isolated via centrifugation, resuspended using 1 mLof diethyl ether, collected via vacuum filtration and washed with approximately 5 mL of diethyl ether. The product was dried invacuo. Off-white powder obtained: 63.1 mg (53.8% yield). MS (acetonitrilewith NaI) calculated molecular mass of C20H42N2O4Cl2Pt: 640.54 g/mol, observed average molecular mass: 640.46 g/mol. 1H NMR (300 MHz, DMF-d7), d (ppm) = 0.85 (6H, m), 1.22 (21H,m), 1.60 (1H, m), 1.72 (2H, m), 2.17 (2H, m), 2.25 (4H, m), 3.00(1H, m), 7.04 (3H, b), 7.60 (2H, b).
  • 67
  • [ 626-27-7 ]
  • coniferal alcohol [ No CAS ]
  • (2E)-3-(4-O-heptanoyl-3-methoxyphenyl)prop-2-en-1-yl heptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 24h; General procedure: Coniferol (1e, 100 mg) was dissolved in amixture of pyridine (3.0 mL) and anhydride (1e,1.5 mL), then the mixture was allowed to stand at room temperature for 24 h. After the addition of 10 mL of water, the resulting mixture was partitioned with EtOAc. The EtOAc partition was evaporated to dryness and then separated by HPLC (column B, mobile phase: MeOH-H2O in different ratio) to give the desired compounds
  • 68
  • [ 626-27-7 ]
  • [ 496-73-1 ]
  • 1-(2,4-dihydroxy-5-methylphenyl)heptan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With boron trifluoride diethyl etherate at 90℃; for 16h; 2.1 General procedure for the preparation of acylphenols 2a - 2f and 8a-8f General procedure: 2, 4-dihydroxytoluene (7) was synthesized according to our previously reportedprocedures[1]. To a solution of resorcinol (1) or 2,4-dihydroxytoluene (7) (10 mmol) inBF3.Et2O (12 mL) was added anhydride (20 mmol). The reaction mixture was stirred for 16 hat 90 oC and . After cooling, the mixture was neutralized with 100 mL saturated aqueousNaHCO3 and diluted with 200 mL ethyl acetate (EA). The combined organic phase wasfiltered, extracted with EA (3 x 30 mL), dried over anhydrous MgSO4 and concentrated invacuo. The crude product was purified by CC on silica gel eluting with PE-EA (15: 1 - 5: 1)to afford compounds 2a - 2f, 8a - 8f.
73% With boron trifluoride diethyl etherate at 90℃; for 2h; GeneralSynthetic Procedure for Compounds 2a-2h bymethod A General procedure: Amixture of 2,4-dihydroxytoluene (124 mg, 1 mmol), respective acid anhydride(1.2 mmol) andborontrifluoride-diethyl ether (5 mL) was refluxed at 90 °C for 2 h. Reactionmixture was poured in crushed ice and stirred for 10 min and then extractedwith ethyl acetate. Ethyl acetate layer was washed with brine solution andfinally dried over anhydrous sodium sulphate. Solvent was removed under reducedpressure and crude product was purified by silica gel column chromatography(200-300 mesh) using petroleum ether and EtOAc (15:1, v/v) as eluent to givetarget compounds.
  • 69
  • [ 626-27-7 ]
  • C15H14N2O3 [ No CAS ]
  • C27H36N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With dmap; triethylamine In dichloromethane at 20℃; for 8.5h; Inert atmosphere; General Procedure for the Acylation of Indolyl Nitrogen(General Procedure B) General procedure: To a stirred solution of 16 (10 mg, 0.040 mmol) and triethylamine(13 mg, 0.55 mmol) in CH2Cl2 (0.40 mL) at room temperature was added dropwise acetyl anhydride (9.8 mg,0.10 mmol), via a syringe, followed by DMAP (0.45 mg,0.0040 mmol). The mixture was stirred at room temperaturefor 8.5 h and then poured into an aqueous solution of NH4Cl.The aqueous layer was separated and extracted with AcOEt.The organic solution was washed with brine, dried overNa2SO4, and concentrated under reduced pressure. The residuewas purified by silica gel column chromatography (SiO2, eluent: AcOEt-hexane=3 : 10-7 : 10) to give 17a as a white powder (9.7 mg, 84%).
  • 70
  • [ 626-27-7 ]
  • 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 3,4,6-tri-O-hexanoyl-β-D-mannopyranoside [ No CAS ]
  • 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 2-O-heptanoyl-3,4,6-tri-O-hexanoyl-β-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With pyridine; dmap In dichloromethane at 20℃; for 20h; 3.1.20 Esterification of tetrakisalcohol (21) General procedure: To a solution of 21 (66.7mg, 0.124mmol) and DMAP (60.6mg, 0.496mmol) in a mixture of CH2Cl2 (1.2mL) and pyridine (50μL, 0.620mmol) was added propionyl chloride (54μL, 0.620mmol) at room temperature, and the reaction mixture was stirred at room temperature for 20h. After the reaction was quenched with water, the resulting mixture was extracted with CH2Cl2. The extract was successively washed with aqueous sodium bicarbonate, water and brine, and concentrated in vacuo. The residue was purified by means of column chromatography (n-hexane-EtOAc, 12/1) to give 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-d-mannitol-1-yl 2,3,4,6-tetra-O-propanoyl-β-d-mannopyranoside (22d, 89.1mg, 94%).
  • 71
  • [ 626-27-7 ]
  • [ 1418269-49-4 ]
  • 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 3,4,6-tri-O-heptanoyl-2-O-octanoyl-β-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With pyridine; dmap In dichloromethane at 20℃; for 20h; 3.1.20 Esterification of tetrakisalcohol (21) General procedure: To a solution of 21 (66.7mg, 0.124mmol) and DMAP (60.6mg, 0.496mmol) in a mixture of CH2Cl2 (1.2mL) and pyridine (50μL, 0.620mmol) was added propionyl chloride (54μL, 0.620mmol) at room temperature, and the reaction mixture was stirred at room temperature for 20h. After the reaction was quenched with water, the resulting mixture was extracted with CH2Cl2. The extract was successively washed with aqueous sodium bicarbonate, water and brine, and concentrated in vacuo. The residue was purified by means of column chromatography (n-hexane-EtOAc, 12/1) to give 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-d-mannitol-1-yl 2,3,4,6-tetra-O-propanoyl-β-d-mannopyranoside (22d, 89.1mg, 94%).
  • 72
  • [ 626-27-7 ]
  • [ 1415557-41-3 ]
  • C52H94O15Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With pyridine; dmap In dichloromethane at 20℃; for 20h; 3.1.20 Esterification of tetrakisalcohol (21) General procedure: To a solution of 21 (66.7mg, 0.124mmol) and DMAP (60.6mg, 0.496mmol) in a mixture of CH2Cl2 (1.2mL) and pyridine (50μL, 0.620mmol) was added propionyl chloride (54μL, 0.620mmol) at room temperature, and the reaction mixture was stirred at room temperature for 20h. After the reaction was quenched with water, the resulting mixture was extracted with CH2Cl2. The extract was successively washed with aqueous sodium bicarbonate, water and brine, and concentrated in vacuo. The residue was purified by means of column chromatography (n-hexane-EtOAc, 12/1) to give 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-d-mannitol-1-yl 2,3,4,6-tetra-O-propanoyl-β-d-mannopyranoside (22d, 89.1mg, 94%).
  • 73
  • [ 626-27-7 ]
  • [ 108-95-2 ]
  • [ 56052-14-3 ]
YieldReaction ConditionsOperation in experiment
90% With magnesium monohydroxide; di-<i>tert</i>-butyl dicarbonate; lithium chloride at 25℃; for 6h; 1 Example 1 In a 100 mL flask, 6.120 g (23.99 mmol) of heptanoic anhydride, 5.342 g (23.99 mmol) of di-t-butyl dicarbonate, (0.23 mmol, 0.5 mole%) and 0.010 g of lithium chloride (0.5 mol%) were added to the reaction mixture in the same manner as in Example 1, (0.23 mmol, 0.5 mol%) were sequentially added, and the reaction was not carried out at 25 ° C under stirring. Heptanoic acid was prepared in the same manner as in Example 1. Table 1 shows the reaction results at 3 hours or 6 hours after the start of the reaction.
80% With magnesium hydroxide at 25℃; for 17h; 30 Example 30 In a 50 mL-volume eggplant-shaped flask, 1.500 grams (11.5 mmol) of heptanoic acid, 1.283 grams (5.8 mmol) of di-t-butyl dicarbonate, 0.125 grams (0.2 mmol, 4 mol % relative to di-t-butyl dicarbonate) of magnesium carbonate hydroxide were added successively. Reactions were carried out for 12 hours at 25° C. while the mixture was being stirred. The mixture containing heptanoic acid anhydride was diluted with ethyl acetate and washed with pure water. The washed mixture was separated into an organic phase and water phase, and 1.257 grams (5.2 mmol, 90% yield) of heptanoic acid anhydride was obtained by concentrating the organic phase. Into the heptanoic acid anhydride, 0.488 grams (5.2 mmol) of phenol, and 0.015 grams (0.3 mmol, 5 mol % relative to phenol) of magnesium hydroxide were added successively, which was then subjected to reactions at 25° C. while the mixture was being stirred. Accordingly, phenyl heptanoate was produced. The reaction results obtained 17 hours after the start of reactions are shown in Table 2.
  • 74
  • [ 142-62-1 ]
  • [ 626-27-7 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: hexanoic acid With potassium carbonate In water Microwave irradiation; Stage #2: With p-toluenesulfonyl chloride In acetonitrile for 1.5h; Sonication; 3.4. General Procedure for the Preparation of CarboxylicAcid Anhydride Using TsCl Under Ultrasound Irradiation General procedure: A few drops of water were added to the mixture of carboxylic acid (1 mmol) and K2CO3 (1.5 mmol, 0.20 g) and put in MW for 2-4 min (900 W), then dry CH3CN (5 mL) and TsCl (0.5 mmol, 0.10 g) were added. The reaction mixture was allowed to ultrasound irradiation for suitable time. After the completion of the reaction, CH2Cl2 or Et2O(2×10 mL) was added to the reaction mixture, stirred, filtered, and the organic layer was dried over CaCl2. The evaporation of the solvent afforded a highly pure product.
  • 75
  • [ 626-27-7 ]
  • [ 701231-79-0 ]
YieldReaction ConditionsOperation in experiment
With sodium azide In acetonitrile for 1.75h; Sonication; 3.5. General Procedure for the Preparation of Acyl AzideFrom Produced Carboxylic Anhydrides and Sodium Azide General procedure: After the completion of the synthesis of carboxylic anhydride(the TsCl disappeared completely, monitored by TLC),NaN3 (0.7 mmol, 0.05 g) and CH3CN (2 mL) were added tothe reaction mixture and the mixture subjected to ultrasound irradiation for the appropriate time (Table 6) until the carboxylic anhydride disappeared completely (monitored byTLC). After the completion of the reaction, CH2Cl2 or Et2O(2×10 mL) was added to the reaction mixture, stirred, filtered,and the organic layer was dried over CaCl2. The evaporation of the solvent afforded a highly pure product.
  • 77
  • [ 626-27-7 ]
  • [ 120014-06-4 ]
  • donepezil enanthate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.7% Stage #1: n-heptanoic anhydride; donepezil With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 10℃; Inert atmosphere; Stage #2: In tetrahydrofuran at -78 - 30℃; 3 Compound 3: Preparation of Donepezil Heptanoate The preparation process was the same as that of Example 2. Donepezil (40.0 g, 105.4 mmol) was reacted with heptanoic anhydride (38.82 g, 242.4 mmol) to obtain 42.30 g of donepezil heptanoate (yield: 81.7%) with HPLC (aera): 98.2%. (0038) Mass spectrum (m/z): [M+H]+=492.4. (0039) 1H-NMR (CDCl3) δ: 7.32-7.31 (4H, d), 7.26-7.27 (1H, m), 6.98 (1H, s), 6.59 (1H, s), 3.89 (3H, s), 3.90 (3H, s), 3.50 (2H, s), 3.26 (2H, s), 2.87-2.89 (2H, d), 2.60-2.64 (2H, t), 2.27-2.29 (2H, d), 1.90-1.93 (2H, t), 1.80-1.83 (2H, t), 1.65-1.68 (2H, t), 1.20-1.60 (9H, m), 0.90-0.96 (3H, t).
  • 78
  • [ 111-70-6 ]
  • [ 111-71-7 ]
  • [ 626-27-7 ]
YieldReaction ConditionsOperation in experiment
1: 30.9 %Chromat. 2: 62 %Chromat. With 2,6-dimethylpyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; sodium hydrogencarbonate; potassium iodide In dichloromethane; water Electrolysis; General procedure of alcohols oxidation. General procedure: Electrolysis was performed in a membrane-free 150 mLelectrolyzer equipped with a water jacket, thermometer,and mechanical stirrer. Anode (20 cm2) andcathode (10 cm2) were made of platinum plates.Alcohol (0.04 mol), 4-acetylamino-2,2,6,6-tetramethylpiperidin-1-oxyl (0.004 mol, 0.85 g), and0.004 mol of the corresponding pyridine basedissolved in 40 mL of methylene chloride were put inthe electrolyzer. 0.06 mol (5.0 g) of NaHCO3 and0.01 mol (1.7 g) of KI dissolved in 80 mL of distilledwater ( of the aqueous phase 8.6) were then added.The synthesis was performed at current density 0.05 A/cm2(current 1 A) and was complete after passing 6 F/molof electricity. After the reaction was complete, theelectrolyte was treated with concentrated solution ofsodium thiosulfate to remove excess of iodine. Theaqueous and organic layers were separated. Theaqueous layer was acidified with dilute hydrochloricacid to pH 5 and extracted with methylene chloride(2×20 mL); the organic phases were combined andanalyzed by means of gas chromato-mass spectrometryas described elsewhere [1]
  • 79
  • [ 626-27-7 ]
  • C43H65NO7 [ No CAS ]
  • C50H77NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: n-heptanoic anhydride; C43H65NO7 With pyridine In dichloromethane for 2h; Stage #2: With sodium hydroxide In methanol; dichloromethane for 6h; 4.1.10 General procedures B for amide bond coupling and deprotection to afford 41-45 General procedure: Compound 19 (22mg) was diluted with CH2Cl2 (3mL); then, pyridine (0.5mL), and anhydrides (0.1mL) were added. The reaction was stirred for 2h to a mixture of partially acetylated products. The mixture was concentrated, then dissolved in CH2Cl2/MeOH=1/1 (4mL), diluted with 4.0N NaOH (aq) (0.1mL), and stirred for 6h. The mixture was concentrated in vacuo, dissolved in CH2Cl2, washed with NH4Cl and brine, concentrated in vacuo, and purified by flash column chromatography (silica gel; CH2Cl2/MeOH=18/1) to get deacylated products 22-26. Then, the deacylated products were dissolved in MeOH and 10% Pd/C was added. The mixture was stirred under H2 at room temperature for 8h. The residue was filtered, concentrated in vacuo, and purified by flash column chromatography (silica gel; CH2Cl2/MeOH=14/1).
  • 80
  • [ 626-27-7 ]
  • [ 109-79-5 ]
  • [ 116074-61-4 ]
YieldReaction ConditionsOperation in experiment
52% With magnesium monohydroxide; di-<i>tert</i>-butyl dicarbonate; sodium carbonate at 25℃; for 24h; 4 Example 4 General procedure: In a flask with a capacity of 100 mL heptanoic anhydride 7.426 g (29.11 mmol) , Di-t-butyl dicarbonate 6.483 g (29.11 mmol), And 1-butanethiol 5.000 g (55.44 mmol), Are sequentially added, To obtain a homogeneous solution. To this reaction mixture was added magnesium hydroxide 0.016 g (0.28 mmol, 0.5 mol%) And lithium hydroxide monohydrate 0.012 g (0.28 mmol, 0.5 mol%) Are sequentially added, With stirring, The reaction was carried out at 25 ° C., S-butyl thioheptanoate was produced. The results of the reaction 24 hours after the start of the reaction are shown in Table 1
  • 81
  • [ 626-27-7 ]
  • [ 1370794-63-0 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: n-heptanoic anhydride With triethylamine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With ammonium-<SUP>15</SUP>N hydrochloride In dichloromethane; water at 20℃; Inert atmosphere;
  • 82
  • [ 626-27-7 ]
  • [ 35779-04-5 ]
  • 4-tert-Butylhexylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With pyridine N-oxide; [2,2]bipyridinyl; potassium fluoride; lithium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 0 - 25℃; for 24h;
  • 83
  • [ 53261-25-9 ]
  • [ 626-27-7 ]
  • C14H32Cl2N2O4Pt [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine at 70℃; for 3h; 3 Example 3 Synthesis of CDDP prodrug 2 containing a saturated alkane chain compound, as shown in Figure 3: Add II (100 mg, 0.3 mmol) and n-heptanoic anhydride (146 mg, 0.6 mmol) to a 100 mL round bottom flask, and dissolve in 2 mL of anhydrous dimethylformamide (DMF).1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.3 mmol) was added. After stirring at 70 ° C for 3 hours, water was added to precipitate to give a slightly yellow solid; then washed with water and petroleum ether and filtered to give product 2 (109 mg, yield 65%).
  • 84
  • [ 626-27-7 ]
  • [ 122948-47-4 ]
  • C18H26 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With pyridine N-oxide; potassium fluoride; 1,10-Phenanthroline; lithium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 0℃; for 72h; Inert atmosphere; Sealed tube;
  • 85
  • [ 626-27-7 ]
  • 4-cyano-3,5-dimethylphenyl trifluoromethanesulfonate [ No CAS ]
  • 2,6-dimethyl-4-n-hexyl benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With pyridine N-oxide; potassium fluoride; 1,10-Phenanthroline; lithium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 30℃; for 48h; Inert atmosphere; 4.2. Representative procedure for the preparation ofdecarboxylative coupling products 3 General procedure: To a flamed dried 15.00mL round flask was added NiCl2(0.075 mmol, 0.15 equiv), 1, 10-phenanthroline (0.075 mmol, 0.15equiv), DMAc (2.00 mL). The mixture was stirred at room temperaturefor 1 h in glove box. Then, aryl triflates (0.50 mmol, 1.00equiv), anhydrides (1.25 mmol, 2.50 equiv), pyridine N-oxide(1.25 mmol, 2.50 equiv), LiCl (2.50 mmol, 5.00 equiv), KF (0.75 mmol, 1.50 equiv), zinc powder (1.50 mmol, 3.00 equiv) andDMAc (3.00 mL) were added to the solution successively. The flaskwas capped with a screw cap fitted with a PTFE-faced siliconeseptum, removed from the glove box and stirred at 0 C (or 30 C)for 72 h (or 48 h). When the reaction was completed, the resultingmixture was poured into ethyl acetate (150.00 mL), washed withwater and brine twice, dried over Na2SO4, concentrated underreduced pressure, the crude residue was then purified by a flashcolumn chromatography.
  • 86
  • [ 111-14-8 ]
  • [ 2528-61-2 ]
  • [ 626-27-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: oenanthic acid With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: Heptanoic acid chloride In dichloromethane at 0 - 20℃; B: Synthesis of Alkyl Acid Anhydrides General procedure: To a flamed-dried flask with magnetic stir bar, was added aliphatic acid (1.0 equiv), dried DCM (1.0 M) and triethylamine (1.05 equiv) successively. The solution was stirred for 30 minutes at 0 0C. Then acyl chloride (1.05 equiv) was added dropwise to the mixture and stirred overnight at rt. The solvent was evaporated by vacuum to afford the crude mixture. And the mixture was dissolved in n-hexane. Then the residue was filtered through a small plug of celite and concentrated to afford the anhydrides. This product was used to next catalytic reaction without any further purification.
  • 87
  • [ 626-27-7 ]
  • curcumin [ No CAS ]
  • C28H32O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.7% With pyridine; dmap In dichloromethane at 20℃; for 2.16h; Cooling with ice; 5 Preparation of intermediate 5-1 curcumin monoheptanoate Under ice bath conditions,Curcumin 10g (27.14mmol), 10.73g pyridine (135.70mmol),0.33g DMAP (2.70 mmol)And 200mL DCM was added to the three-neck reaction flask.Then it will contain 5.81g (21.52mmol) of heptanoic anhydride.20mLDCM solution is dropped into the system,The addition was completed in about 10 minutes.Then, the temperature was naturally raised to room temperature for 2 hours.Stop the reaction and pass the reaction solution to 100 mL of 1N hydrochloric acid.Wash with 100mL of water,Divided into DCM solution,Dry over anhydrous sodium sulfate, filter and concentrate to give a crude.Silica gel column chromatography gave a yellow solid ( 4.40 g, yield: 33.7%).
  • 88
  • [ 626-27-7 ]
  • donepezil [ No CAS ]
  • donepezil enanthate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.7% Stage #1: donepezil With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -60℃; Inert atmosphere; Stage #2: n-heptanoic anhydride In tetrahydrofuran at -78 - -60℃; for 0.5h; Inert atmosphere; 1 Preparation of compound 1 donepezil enanthate Add donepezil (40.0g, 105.4mmol) to a 1000ml three-neck round bottom flask (equipped with argon protection, thermometer, mechanical stirring, constant pressure dropping funnel), replace with nitrogen, add 300ml of anhydrous tetrahydrofuran, stir to dissolve, and then dissolve Cool to -60 to -78 ° C. Add lithium bistrimethylsilylamine (100ml, 1.0mol / L, 100mmol) into the constant-pressure dropping funnel through a double-ended needle, and add it quickly at one time. Stir for 15-30 minutes at -60 -78 . After that, the temperature was naturally raised to 0 to 10 ° C.Subsequently, the temperature of the system was reduced to -60 to -78 ° C, and then heptanoic anhydride (38.82g, 242.4mmol) was dissolved in 100 ml of anhydrous tetrahydrofuran and added to a constant-pressure dropping funnel, and was added quickly at a time, -60 to -78 ° C. After stirring for 30 minutes, the temperature was naturally raised to room temperature (20-30 ° C), and the reaction of the raw materials was detected by TLC.250 ml of saturated ammonium chloride solution was added dropwise to the reaction system in an ice-water bath. After the addition was completed, the liquid was separated, and then washed with 250 ml of a 20% sodium chloride solution, and washed with 250 ml of a saturated sodium chloride solution. The phases were dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 29.3 g of an oil (yield: 93%). The oily substance was dissolved by heating with 225 ml of n-heptane and filtered to remove insoluble matter, then 22.5 ml of ethanol was added, and the temperature was reduced to crystallize. The temperature was maintained at -5 to -10 ° C for 1 h, filtered, and cold n-heptane / ethanol (10: 1 ) Washed with 50 ml, dried by suction, and dried under vacuum to obtain 42.30 g (yield: 81.7%) as an off-white solid.
  • 89
  • [ 626-27-7 ]
  • benzyl 3(β)-hydroxy-23-(t-butyldimethylsilyloxy)olean-12-en-28-oate [ No CAS ]
  • 28-O-benzyl 3-O-(2′-heptanoylamino-2′-deoxy-β-D-glucopyranosyl)quillaic ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: benzyl 3(β)-hydroxy-23-(t-butyldimethylsilyloxy)olean-12-en-28-oate With acetic acid; zinc In dichloromethane for 8h; Stage #2: n-heptanoic anhydride With triethylamine In dichloromethane for 8h; 4.1.8. 28-O-Benzyl 3-O-(2′-heptanoylamino-2′-deoxy-β-D-glucopyranosyl)quillaic ester (22) Zinc (355 mg, 5.44 mmol) was added to a solution of compound 21(171 mg, 0.165 mmol) in CH2Cl2/AcOH = 1/1 (2 mL). After 8 h, the mixture was filtered, washed with NaHCO3 solution and brine, and concentrated in vacuo. The residue was purified by column chromatography and proceeded to next step. Heptanoic anhydride (46 μL,0.18 mmol) and triethylamine (23 μL, 0.17 mmol) were added to asolution of product (76.0 mg, 0.0880 mmol) in CH2Cl2 (2 mL). After 8 h, the mixture was concentrated in vacuo and purified by columnchromatography (silica gel; CH2Cl2/MeOH = 12/1) to give compound 22 (45.9 mg, 0.0540 mmol, 61%); 1H NMR (400 MHz, CD3OD/CDCl3 = 4/1) δ 9.31 (s, 1H, H-23), 7.38-7.23 (m, 5H, Ar-H), 5.28 (bs,1H, H-12), 5.01 (s, 2H, CO2CH2Ph), 4.46 (bs, 1H, H-16), 4.30 (d,J = 8.3 Hz, 1H, H-1′), 3.84 (dd, J = 11.9, 2.2 Hz, 1H, H-6a'), 3.75 (dd,J = 11.9, 4.6 Hz, 1H, H-3), 3.67 (dd, J = 11.9, 5.4 Hz, 1H, H-6b'), 3.54(dd, J = 10.1, 8.3 Hz, 1H, H-2′), 3.36 (dd, J = 10.1, 8.6 Hz, 1H, H-3′),3.29 (m, J = 8.6 Hz, 1H, H-4′), 3.22 (ddd, J = 9.3, 5.4, 2.2 Hz, 1H, H-5′), 3.02 (dd, J = 14.1, 3.8 Hz, 1H, H-18), 2.32-2.15 (m, 3H,),2.05-1.96 (m, 1H,), 1.95-1.80 (m, 4H), 1.79-1.72 (m, 1H), 1.71-1.56(m, 6H), 1.56-1.36 (m, 4H), 1.35 (s, 3H), 1.34-1.30 (m, 5H), 1.30-1.21(m, 3H), 1.19-1.10 (m, 2H), 1.09-1.01 (m, 2H), 1.00 (s, 3H), 0.94 (s,3H), 0.93 (s, 3H), 0.92-0.87 (m, 4H), 0.87 (s, 3H), 0.53 ppm (s, 3H);13C NMR (100 MHz, CD3OD/CDCl3 = 4/1): δ 208.0 (C-23), 178.2(COCH2Ph), 176.4 (NC = O), 144.4 (C-13), 137.1, 129.2, 129.1, 129.0,123.2 (C-12), 103.4 (C-1′), 83.1 (C-3), 77.3 (C-16), 75.5 (C-5′), 74.8 (C-3′), 71.8 (C-4′), 67.2 (COCH2Ph), 62.5 (C-6′), 57.0 (C-2′), 56.1, 48.8,47.7, 47.3, 42.4, 41.9, 40.6, 39.0, 37.2, 36.6, 36.2, 35.8, 33.2, 32.5,32.2, 31.2, 29.9, 27.1, 26.3, 25.6, 24.8, 24.1, 23.4, 21.2, 17.5, 16.1,14.4, 10.3 ppm; HRMS (ESI TOF-MS) [M + H]+: calcd. forC50H76NO10 + H: 850.5423; found: 850.5412
  • 90
  • [ 626-27-7 ]
  • C43H65NO8 [ No CAS ]
  • 3-O-(2′-heptanoylamino-2′-deoxy-β-D-glucopyranosyl)hederagenin [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: n-heptanoic anhydride; C43H65NO8 With triethylamine In dichloromethane for 8h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 8h; 4.1.5. 3-O-(2′-Heptanoylamino-2′-deoxy-β-D-glucopyranosyl) hederagenin(17) Heptanoic anhydride (44 μL, 0.17 mmol) and triethylamine (23 μμL,0.17 mmol) were added to a solution of 13 (20.0 mg, 0.0276 mmol) in CH2Cl2 (1 mL). After 8 h, the mixture was concentrated in vacuo, redissolved in MeOH, added NaHCO3 (27 mg, 0.33 mmol), and stirred for 8 h. After completion, Amberlite H +was added for neutralization, and the mixture was filtered, concentrated, purified by column chromatography (silica gel; CH2Cl2/MeOH = 12/1). 10% Pd/C (3.0 mg) was added to the solution of product (9.0 mg, 0.011 mmol) in MeOH (1 mL).The mixture was stirred under H2 (balloon) at room temperature for 8 h. The residue was filtered, concentrated in vacuo and purified by column chromatography (silica gel; CH2Cl2/MeOH = 8/1) to give compound 17 (5.0 mg, 0.0067 mmol, 61%) m.p. 226 °C; 1H NMR(600 MHz, CD3OD/CDCl3= 4/1) δ 5.24 (t, J = 3.6 Hz, 1H, H-12), 4.44(d, J = 8.3 Hz, 1H, H-1′), 3.84 (dd, J = 12.1, 2.5 Hz, 1H, H-6a'),3.75-3.67 (m, 2H, H-6b', H-2′), 3.57 (dd, J = 11.9, 4.7 Hz, 1H, H-3),3.39-3.32 (m, 3H, H-23a, H-4′, H-3′), 3.28-3.20 (m, 2H, H-23b, H-5′),2.83 (dd, J = 14.1, 3.7 Hz, 1H, H-18), 2.28-2.16 (m, 2H), 1.92-1.85(m, 2H), 1.76-1.71 (m, 2H), 1.64-1.59 (m, 5H), 1.55-1.51 (m, 1H),1.34-1.30 (m, 6H), 1.29-1.27 (m, 6H), 1.24-1.20 (m, 2H), 1.16 (s, 3H),1.15-1.13 (m, 1H), 1.13-1.00 (m, 3H), 0.95 (s, 3H), 0.94 (s, 3H), 0.90(s, 6H), 0.80 (s, 3H), 0.60 ppm (s, 3H); 13C NMR (150 MHz, CD3OD/CDCl3 = 4/1): δ 181.8 (COOH), 176.3 (NC = O), 145.0 (C-13), 123.4(C-12), 104.3 (C-1′), 82.8 (C-3), 77.2 (C-5′) , 76.3 (C-3′), 71.9 (C-4′),64.3 (C-23), 62.6 (C-6′), 57.1 (C-2′), 47.6, 47.4, 47.0, 43.7, 42.8, 42.5,40.3, 39.2, 37.4, 37.4, 34.8, 33.6, 33.5, 33.2, 32.9, 32.6, 31.5, 30.6,30.3, 30.1, 28.6, 26.6, 26.4, 26.2, 24.4, 24.0, 23.9, 23.6, 23.4, 18.6,17.6, 16.3, 14.4, 13.5 ppm; HRMS (ESI TOF-MS) [M + H]+: calcd. forC43H72NO9 + H: 746.5202; found: 746.5210; HPLC purity 95.6% (tR:7.1 min, Mightysil, RP-18, 250 × 4.6 mm, 5 mm, H2O/ACN = 30/70,1 mL/min, 30 min)
  • 91
  • [ 626-27-7 ]
  • C43H65NO8 [ No CAS ]
  • 3-O-(2′-heptanoylamino-2′-deoxy-β-D-glucopyranosyl)echinocystic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: n-heptanoic anhydride; C43H65NO8 With triethylamine In dichloromethane for 4h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h; 4.1.6. 3-O-(2′-Heptanoylamino-2′-deoxy-β-D-glucopyranosyl) echinocysticacid (18) Heptanoic anhydride (128 μL, 0.486 mmol) and triethylamine (68 μL, 0.48 mmol) were added to a solution of compound 14 (59 mg,0.082 mmol) in CH2Cl2 (2 mL). After 4 h, the mixture was concentrated in vacuo, redissolved in MeOH, added NaHCO3 (27 mg, 0.33 mmol),and stirred for 8 h. After completion, Amberlite H + was added for neutralization, and the mixture was filtered, concentrated in vacuo,purified by column chromatography (silica gel; CH2Cl2/MeOH = 12/1). The product was dissolved in MeOH (2 mL), and 10% Pd/C (5.0 mg)was added to the solution, stirred under H2 (balloon) at room temperature for 12 h. The residue was filtered, concentrated in vacuo and purified by column chromatography (silica gel; CH2Cl2/MeOH = 10/1) to give compound 18 (21.0 mg, 0.0281 mmol, 50%). m.p. 219 °C; 1HNMR (400 MHz, CD3OD/CDCl3 = 4/1) δ 5.27 (t, J = 3.3 Hz, 1H, H-12), 4.45-4.41 (m, 2H, H-16, H-1′), 3.82 (dd, J = 12.0, 2.4 Hz, 1H, H-6a'), 3.70-3.62 (m, 2H, H-6b', H-2′), 3.41 (dd, J = 10.2, 9.0 Hz, 1H, H-3′), 3.31 (t, J = 9.0 Hz, 1H, H-4′), 3.22 (ddd, J = 9.0, 5.2, 2.4 Hz, 1H,H-5′), 3.08 (dd, J = 11.9, 4.5 Hz, 1H, H-3), 2.97 (dd, J = 14.3, 4.0 Hz,1H, H-18), 2.28-2.20 (m, 1H,), 2.17 (td, J = 8.2, 3.6 Hz, 1H, H-2′'),1.93-1.83 (m, 5H), 1.82-1.76 (m, 1H), 1.75-1.66 (m, 1H), 1.64-1.56(m, 4H), 1.54-1.44 (m, 2H), 1.38-1.31 (m, 6H), 1.31-1.21 (m, 7H),1.18-1.06 (m, 1H), 1.04-0.95 (m, 2H), 0.93 (s, 6H), 0.90 (s, 3H),0.89-0.86 (m, 3H), 0.85 (s, 3H), 0.75 (s, 3H), 0.73 (s, 3H),0.72-0.69 ppm (m, 1H); 13C NMR (100 MHz, CD3OD/CDCl3 = 4/1): δ181.0 (COOH), 176.2 (NC = O), 144.7 (C-13), 123.2 (C-12), 104.6 (C-1′), 90.7 (C-3), 77.2 (C-16), 75.8 (C-5′), 75.0 (C-3′), 72.0 (C-4′), 62.6 (C-6′), 57.4 (C-2′), 56.8, 47.9, 47.4, 42.4, 41.8, 40.4, 39.8, 39.6, 37.7,37.4, 36.3, 36.0, 34.0, 33.3, 32.5, 32.3, 31.2, 30.0, 28.7, 27.2, 26.7,26.5, 24.9, 24.3, 23.4, 19.2, 17.6, 17.0, 16.0, 14.4 ppm; HRMS (ESITOF-MS) [M + H]+: calcd. for C43H72NO9 + H: 746.5202; found:746.5215; HPLC purity 96.6% (tR: 7.3 min, Mightysil, RP-18,250 × 4.6 mm, 5 mm, H2O/ACN = 30/70, 1 mL/min, 30 min)
  • 92
  • [ 626-27-7 ]
  • [ 108-46-3 ]
  • [ 27883-47-2 ]
YieldReaction ConditionsOperation in experiment
86% With boron trifluoride diethyl etherate at 90℃; for 16h; 2.1 General procedure for the preparation of acylphenols 2a - 2f and 8a-8f General procedure: 2, 4-dihydroxytoluene (7) was synthesized according to our previously reportedprocedures[1]. To a solution of resorcinol (1) or 2,4-dihydroxytoluene (7) (10 mmol) inBF3.Et2O (12 mL) was added anhydride (20 mmol). The reaction mixture was stirred for 16 hat 90 oC and . After cooling, the mixture was neutralized with 100 mL saturated aqueousNaHCO3 and diluted with 200 mL ethyl acetate (EA). The combined organic phase wasfiltered, extracted with EA (3 x 30 mL), dried over anhydrous MgSO4 and concentrated invacuo. The crude product was purified by CC on silica gel eluting with PE-EA (15: 1 - 5: 1)to afford compounds 2a - 2f, 8a - 8f.
  • 93
  • [ 626-27-7 ]
  • [ 162062-88-6 ]
  • (20S,24R)-epoxy-12β, 25-dihydroxy-(3β-O-heptanoyl)-dammarane [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.5% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4h;
  • 94
  • [ 626-27-7 ]
  • 3-amino-1-(4-fluorobenzyl)-4-methylpyridin-2(1H)-one [ No CAS ]
  • N-(1-(4-fluorobenzyl)-4-methyl-2-oxo-1,2- dihydropyridin-3-yl)-heptanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% In toluene at 110℃; for 16h; 4.1.4 General procedure for the synthesis of compounds 27-29 The suitable anhydride (1.32mmol) was added to a solution of compound 10 (0.255g, 1.01mmol) in toluene (2.75mL) and the reaction mixture, was stirred for 16hat 110°C. The solvent was evaporated under reduced pressure. The residue obtained was dissolved in CHCl3 and washed three times with water. The organic phase was then dried over Na2SO4, filtered and concentrated in vacuum.
  • 95
  • [ 626-27-7 ]
  • C18H29N2O2(1+)*Br(1-) [ No CAS ]
  • C25H41N2O3(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.8% With pyridine at 90℃; Sealed tube; 34 385 mg IM-11 was mixed with 1 mL n-heptanoic anhydride, 3 mL pyridine was added, and the tube was sealed and reacted overnight at 90°C. After cooling, the solvent was evaporated under reduced pressure, and ethyl acetate was added to precipitate a powdery solid. It was filtered to obtain a white solid powder, which was recrystallized twice with ethyl acetate/ethanol to obtain 168 mg of a white solid powder, namely compound 34, with a yield of 33.8%.
  • 96
  • [ 626-27-7 ]
  • C16H27N2O2(1+)*Cl(1-) [ No CAS ]
  • C23H39N2O3(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With pyridine at 90℃; for 8h; Sealed tube; 12 Example 12 Mix 315 mg of compound 1 with 1 mL of n-heptanoic anhydride, add 3 mL of pyridine, seal the tube and stir at 90°C for 8 hours, evaporate the pyridine under reduced pressure, and add ethyl acetate to precipitate a powdery solid. It was filtered to obtain a white solid powder, which was recrystallized twice with ethyl acetate/ethanol to obtain 141 mg of a white solid powder, namely compound 12, with a yield of 33%.
  • 97
  • [ 626-27-7 ]
  • [ 2113-51-1 ]
  • 10-pentylphenanthren-9-yl heptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: n-heptanoic anhydride; 2-iodobiphenyl With oenanthic acid; palladium diacetate; potassium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With triethylamine In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere;
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