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[ CAS No. 3303-31-9 ] {[proInfo.proName]}

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Chemical Structure| 3303-31-9
Chemical Structure| 3303-31-9
Structure of 3303-31-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3303-31-9 ]

CAS No. :3303-31-9 MDL No. :MFCD00065185
Formula : C12H24N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LCPYQJIKPJDLLB-UWVGGRQHSA-N
M.W : 244.33 Pubchem ID :76807
Synonyms :
L-Leucyl-L-leucine

Calculated chemistry of [ 3303-31-9 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 67.28
TPSA : 92.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : -1.46
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 0.56

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.09
Solubility : 303.0 mg/ml ; 1.24 mol/l
Class : Highly soluble
Log S (Ali) : 0.02
Solubility : 258.0 mg/ml ; 1.05 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.45
Solubility : 8.59 mg/ml ; 0.0352 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.69

Safety of [ 3303-31-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3303-31-9 ]

* 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 [ 3303-31-9 ]

[ 3303-31-9 ] Synthesis Path-Downstream   1~74

  • 2
  • [ 109068-10-2 ]
  • [ 3303-31-9 ]
  • 3
  • [ 3504-37-8 ]
  • [ 3303-31-9 ]
  • 6
  • <i>N</i>-[<i>N</i>-(4-nitro-benzyloxycarbonyl)-L-leucyl]-L-leucine [ No CAS ]
  • [ 3303-31-9 ]
  • 7
  • <i>N</i>-(<i>N</i>,<i>N</i>-phthaloyl-L-leucyl)-L-leucin-ethyl ester [ No CAS ]
  • [ 3303-31-9 ]
  • 8
  • [ 24733-21-9 ]
  • [ 3303-31-9 ]
  • 9
  • [ 116-16-5 ]
  • [ 3303-31-9 ]
  • [ 24299-25-0 ]
  • 10
  • [ 3304-64-1 ]
  • [ 3303-31-9 ]
  • 11
  • [ 3303-31-9 ]
  • [ 80556-22-5 ]
  • C21H34N3O7P [ No CAS ]
  • 12
  • [ 3303-31-9 ]
  • [ 132160-73-7 ]
  • Z-Arg(Z2)-Leu-Leu-OH [ No CAS ]
  • 14
  • [ 2883-36-5 ]
  • [ 3303-31-9 ]
  • [ 17665-02-0 ]
  • 15
  • [ 3303-31-9 ]
  • [ 79-04-9 ]
  • [ 132847-80-4 ]
  • 16
  • [ 3303-31-9 ]
  • [ 82911-69-1 ]
  • [ 88743-98-0 ]
  • 17
  • [ 3303-31-9 ]
  • [ 110661-49-9 ]
  • undecylenyl-L-leucine-L-leucine sodium salt [ No CAS ]
  • 18
  • [ 3303-31-9 ]
  • [ 110661-49-9 ]
  • undecylenyl-L-leucine-L-leucine [ No CAS ]
  • 24
  • <i>N</i>-benzoyl-L-phenylalanyl->leucyl->L-leucine methyl ester [ No CAS ]
  • [ 3303-31-9 ]
  • 25
  • Trt-Leu-Leu-ABAR [ No CAS ]
  • [ 3303-31-9 ]
  • 26
  • Trt-Leu-Leu-DPMR [ No CAS ]
  • [ 3303-31-9 ]
  • 27
  • [ 3303-31-9 ]
  • [ 16917-09-2 ]
  • [ 98-10-2 ]
  • [ 124-38-9 ]
  • [ 590-86-3 ]
  • 28
  • [ 3397-35-1 ]
  • [ 3303-31-9 ]
  • [ 18867-97-5 ]
  • 29
  • C15H24NO5PSi [ No CAS ]
  • [ 3303-31-9 ]
  • 30
  • [ 3303-31-9 ]
  • [ 35661-60-0 ]
  • Fmoc-Leu-Leu-Leu-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With .;enzyme; In water; at 20.0℃; for 48h; A 96 well format was developed to screen large numbers of combinations of reactant ratios and concentrations. The volume of each well was 300ul. Relative amounts of Fmoc/Cbz-amino acids and dipeptide were added on ratios in a range from 0.25:1 to 4:1. Molarities tested were 20 mM (in terms of Fmoc/Cbz-aa). In order to enable this, 10OmM Fmoc/Cbz-aa and 16OmM di-peptide suspensions were produced. Relative quantities of these were added. A set volume of 25ul of enzyme was added at a concentration of 12 mg/ml. Sufficient quantities of distilled water were added to make up to a final volume of 300mum. As an example, to create a 2OmM 1:4 gel, 171.73ul of 14OmM di-leucine, 75ul of 8OmM Fmoc-Leucine, 25ul of enzyme solution, and 28.57ul of water were added to a well. This was then gently mixed with a pipette, and left to react for 48 hours at room temperature. Each reaction was performed in triplicate. Results of the reactions were measured by HPLC, and the degree of conversion of Fmoc/Cbz-amino acid to Fmoc/Cbz-tripeptide was calculated.The results are shown in Fig 4. Fig 4 demonstrates Fmoc-triGlycine (Fmoc-GGG) is produced as it doesn't form a gel. Fmoc-tri-phenylalanine (Fmoc-FFF) and Fmoc-tri-leucine (Fmoc-LLL) both gave yields of over 70% at a 1 :4 ratio (i.e. Fmoc-a is at 2OmM, aa is at a concentration of 8OmM) whereas Cbz-Phe-Phe-Phe-OH gave a yield of 60%. Little Fmoc-triGlycline (Fmoc-GGG) was produced to the natureo f the thermodynamically controlled equilibrium.
  • 32
  • [ 61-90-5 ]
  • (CCl3O)2CO [ No CAS ]
  • [ 3303-31-9 ]
  • 33
  • [ 3303-31-9 ]
  • 3-{(S)-2-[(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-4-methyl-pentanoyl}-7-oxa-3-aza-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester [ No CAS ]
  • 35
  • [ 3303-31-9 ]
  • (3-hydroxy-2-methylbenzoyl)-Leu-Leu-Leu-[methyl (3RS,4RS)-3,4-epoxypiperidine-3-carboxylate] [ No CAS ]
  • 36
  • [ 3303-31-9 ]
  • (1,2,5,6-tetrahydropyridine-3-carbonyl)-Leu-Leu-Leu-[methyl (3RS,4RS)-3,4-epoxypiperidine-3-carboxylate] [ No CAS ]
  • 37
  • [ 3303-31-9 ]
  • 3-[(S)-2-((S)-2-{(S)-2-[(1-tert-Butoxycarbonyl-1,2,5,6-tetrahydro-pyridine-3-carbonyl)-amino]-4-methyl-pentanoylamino}-4-methyl-pentanoylamino)-4-methyl-pentanoyl]-7-oxa-3-aza-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester [ No CAS ]
  • 41
  • [ 83610-39-3 ]
  • [ 3303-31-9 ]
  • 42
  • [ 2666-93-5 ]
  • [ 3303-31-9 ]
  • 43
  • [ 76863-45-1 ]
  • [ 3303-31-9 ]
  • 44
  • [ 2743-60-4 ]
  • [ 3303-31-9 ]
  • 45
  • <i>N</i>-[<i>N</i>-(4-nitro-benzyloxycarbonyl)-L-leucyl]-L-leucine methyl ester [ No CAS ]
  • [ 3303-31-9 ]
  • 47
  • [ 98204-51-4 ]
  • [ 3303-31-9 ]
  • 48
  • [ 131733-31-8 ]
  • [ 3303-31-9 ]
  • 49
  • [ 121394-58-9 ]
  • [ 3303-31-9 ]
  • 50
  • [ 3253-28-9 ]
  • [ 3303-31-9 ]
  • 51
  • [ 6297-57-0 ]
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  • 52
  • [ 101437-29-0 ]
  • [ 3303-31-9 ]
  • 53
  • [ 102322-09-8 ]
  • [ 3303-31-9 ]
  • 54
  • [ 67-56-1 ]
  • [ 3303-31-9 ]
  • [ 6491-83-4 ]
  • 55
  • cobalt(III) oxyhydroxide [ No CAS ]
  • [ 3303-31-9 ]
  • lithium bis(L-leucyl-L-alaninato)cobaltate(III) [ No CAS ]
  • 56
  • [ 3303-31-9 ]
  • [ 639-58-7 ]
  • (triphenyl)Sn(leucylleucine(1-)) [ No CAS ]
  • 57
  • [ 61-90-5 ]
  • [ 3303-31-9 ]
  • [ 57791-42-1 ]
  • [ 62526-43-6 ]
  • [ 10329-75-6 ]
  • [ 18867-82-8 ]
  • penta(leucine) [ No CAS ]
  • 2-(2-{2-[2-(2-{2-[2-(2-amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-4-methyl-pentanoylamino}-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-4-methyl-pentanoylamino}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid [ No CAS ]
  • C54H101N9O10 [ No CAS ]
  • 58
  • [ 72-18-4 ]
  • [ 61-90-5 ]
  • [ 3918-94-3 ]
  • [ 3303-31-9 ]
  • [ 28130-13-4 ]
  • [ 10329-75-6 ]
  • 59
  • [ 61-90-5 ]
  • [ 3303-31-9 ]
  • [ 10329-75-6 ]
  • [ 18867-82-8 ]
  • penta(leucine) [ No CAS ]
  • 60
  • [ 3303-31-9 ]
  • [ 61-90-5 ]
  • 61
  • [ 3303-31-9 ]
  • [ 1176555-48-8 ]
  • [ 1403487-37-5 ]
  • 62
  • [ 3303-31-9 ]
  • [ 144223-30-3 ]
  • [ 1403487-43-3 ]
  • 63
  • LLVVYPWTQRFF [ No CAS ]
  • [ 3303-31-9 ]
  • LVVYPWTQRFF [ No CAS ]
  • VVYPWTQRFF [ No CAS ]
  • LLVVYPWTQRF [ No CAS ]
  • VV-Hemorphin-7 [ No CAS ]
  • rat LVV-hemorphin-7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cathepsin D; In dimethyl sulfoxide; at 37.0℃; for 24h;pH 3.7;Kinetics; General procedure: Peptides 2, 3, 4 and 5 (Table3) were first dissolved in pure DMSO at a concentration of 4mM. Hydrolysis of the peptides was performed in a final volume of 500muL in the presence of 8.3ng/muL of mature CD and the reaction was conducted at 37C in a Radleys reactor. Three different buffers were used to adjust the reaction pH: Sodium acetate buffer (for pH 3.7, pH 4.5 and pH 5.6), Sodium MES Buffer (for pH 5.6, pH 6 and pH 6.5) and Sodium MOPS (for pH 6.5 and pH 6.8). Substrate concentrations were varied from 10muM to 400muM (10muM, 35muM, 70muM, 140muM, 200muM, 400muM). A zero time aliquot (50muL) was removed from the solution prior to enzyme addition. Aliquots were taken over time (0h, 0.5h, 1h, 1.5h, 2h, 4h, 24h, 28h, 34h, 48h, 72h, 120h) and the reaction was stopped by boiling for 5min followed by a 5min centrifugation at 10,000× g. Samples were stored at-20C for at most 48hprior to their analysis by LC/MS-ESI (cf. Section 2.6).
  • 64
  • LLVVFF [ No CAS ]
  • [ 3303-31-9 ]
  • VVFF [ No CAS ]
  • LLVVF [ No CAS ]
  • LVVF [ No CAS ]
  • LVVFF [ No CAS ]
  • Val-Val-Phe [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cathepsin D; In dimethyl sulfoxide; at 37.0℃;pH 3.7;Kinetics; General procedure: Peptides 2, 3, 4 and 5 (Table3) were first dissolved in pure DMSO at a concentration of 4mM. Hydrolysis of the peptides was performed in a final volume of 500muL in the presence of 8.3ng/muL of mature CD and the reaction was conducted at 37C in a Radleys reactor. Three different buffers were used to adjust the reaction pH: Sodium acetate buffer (for pH 3.7, pH 4.5 and pH 5.6), Sodium MES Buffer (for pH 5.6, pH 6 and pH 6.5) and Sodium MOPS (for pH 6.5 and pH 6.8). Substrate concentrations were varied from 10muM to 400muM (10muM, 35muM, 70muM, 140muM, 200muM, 400muM). A zero time aliquot (50muL) was removed from the solution prior to enzyme addition. Aliquots were taken over time (0h, 0.5h, 1h, 1.5h, 2h, 4h, 24h, 28h, 34h, 48h, 72h, 120h) and the reaction was stopped by boiling for 5min followed by a 5min centrifugation at 10,000× g. Samples were stored at-20C for at most 48hprior to their analysis by LC/MS-ESI (cf. Section 2.6).
  • 65
  • [ 35661-60-0 ]
  • [ 3303-31-9 ]
YieldReaction ConditionsOperation in experiment
91% N-Fmoc-L-Leu (5 equiv.) was activated with HBTU/HOBt in DMF, and then added to the Wang resin swollen in DMF, followed by addition of 1.5 equiv. of DIEA. The mixture was shaken mechanically for 1 h at room temperature. The resin was filtered and washed thoroughly with DMF (3 X 50 mL), MeOH (3 X 50 mL), DMF (3 X 50 mL), MeOH (3 X 50 mL) and then dried in vacuum. The completion of coupling reaction was monitored by the ninhydrin test. When necessary, a second coupling was performed under the same condition. The Fmoc group was deprotected by two consecutive 10 min treatments with 20% piperidine/DMF. N-Fmoc-L-Leu was coupled for 1h. Then, the resin was filtered and washed as usual. After removal of N-Fmoc, peptide cleavage was performed using a 95% TFA/water solution for 1 h. Filtration and evaporation gave the crude peptide carboxylate 6 purified by trituration, lyophilized and characterized by HPLC and mass spectrometry.
General procedure: Synthesis protocol for automated solid phase peptide synthesis: Automated solid-phase peptide synthesis was performed in 50 mumol scale. Loading: To a 10 mL syringe reactor with frit and cap were added 1 g of tritylchloride (TCP) resin (1.56 mmol/g) and 7 mL dry DCM. The resin was pre-swollen for 10 min and the solvent was removed by evaporation in vacuum. A mixture of the amino acid (0.6 mmol) and 3 equivalents of DIPEA dissolved in 5 mL dry DCM was added to the resin. The syringe was agitated for 30 min at room temperature. The solution was removed and the resin was washed (2 × 5 mL DMF, 2 × 5 mL DCM). Capping of non-reacted functional groups of the resin was performed with DCM, methanol and DIPEA 80:15:5 (2 × 10 mL, 10 min). After washing (5 × 5 mL DMF), Fmoc-removal was achieved with DMF/piperidine (4:1, 5 mL, 1 × 2 min, 1 × 20 min). After final washing (2 × 5 mL DMF, 1 × 5 mL methanol, 3 × 5 mL DCM), the resin was dried in vacuo. Coupling of Fmoc/tBu-protected amino acids: To 100 mg of the resin (~0.5 mmol/g), a 0.15 M solution of the amino acid in DMF (3 eq relative to resin loading) was added. After addition of a 0.3 M solution of DIPEA in DMF (3 eq) and a 0.15 M solution of HATU in DMF (3 eq), the reaction solution was mixed for 60 min. A second coupling was performed for 60 min. Finally, the resin was washed with DMF (6 × 2.5 mL). Fmoc removal: DMF/piperidine (4:1, 2.5 mL) was added to the resin and mixed for 2.5 min. The procedure was repeated 4 times. The resin was washed with DMF (5 × 2.5 mL), then DCM (5 × 2 mL). Global deprotection: The resin was transferred to a 5 mL syringe with frit and cap. After addition of the cleavage cocktail (TFA, H2O 90:10), the syringe was shaken for 2 h. The cleaving solution was collected and the resin was washed with MeOH (2 × 3 mL). The combined fractions were concentrated in vacuo.
  • 66
  • [ 3303-31-9 ]
  • [ 2127-36-8 ]
  • 67
  • [ 67-56-1 ]
  • [ 3303-31-9 ]
  • [ 13022-42-9 ]
YieldReaction ConditionsOperation in experiment
With acetyl chloride; at 21.0℃; for 3h; General procedure: To the samples a total volume of 360 muL acetyl chloride:methanol (v:v, 60:300 muL) were added in Reacti-Vials sealed and derivatized for 3 h at room temperature (21 C). The excess of reaction mixture was evaporated in a gentle steam of nitrogen. To the dry residues 50 muL trifluoroacetic anhydride (TFAA) and 100 muL dichloromethane (DCM) were added and derivatized for 10 min at room temperature (21 C) and then 5 min at 110 C. The samples were cooled down to room temperature (21 C) and again dried in a steam of nitrogen and finally dissolved in 100 muL DCM.
  • 68
  • [ 10417-94-4 ]
  • [ 3303-31-9 ]
  • [ 657-24-9 ]
  • C12H24N2O3*C4H11N5*C20H30O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In methanol; at 20.0℃; for 5h; A solution of metformin (free base obtained from HCl salt, 10 mmol)), <strong>[3303-31-9]((S)-2-ammonio-4-methylpentanoyl)-L-leucinate</strong> (10 mmol) and eicosapentaenoic acid (10 mmol)) in methanol (20 mL) was stirred at RT for 5 hrs. The solvent was evaporated in vacuo and co-evaporated with THF to dryness to afford compound in quantitative yield as a yellow solid.
  • 69
  • (x)C2HF3O2*C12H24N2O3 [ No CAS ]
  • [ 3303-31-9 ]
  • 70
  • [ 13139-15-6 ]
  • [ 3303-31-9 ]
YieldReaction ConditionsOperation in experiment
99.6% The reaction mixture containing Boc-Leu and ionic liquid based solid support IL-Z at 1.1: 1 mole ratio was charged in a peptide vessel glass reactor in the ionic liquid solvent IL-Solvent under stirring condition with nitrogen flow and/or shaking for 2 to 4 h at a temperature of 37C. At the end of the reaction, the solvent along with excess amino acid was first separated from the solid mass and then separated from the amino acids by extraction using dichlorome thane. The Boc linkage was deprotected by treating with small amount of NaOH in THF and water mixture (2: 1) in the glass reactor under stirring and/or shaking for about 30 min to 4 h, followed by acidification at pH 5.0. Similarly, other C-terminal blocked Fmoc-Gly was attached to the chain under stirring condition with nitrogen flow and/or shaking at room temperature for 2 to 4 h at a temperature of 37C and the Fmoc part was removed by treating with piperidine in dichloromethane solvent under stirring and/or shaking inside the reactor for 5 min to 2 h to obtain a dipeptide, Leu-Gly, attached to the ionic liquid based solid support. Example 7 (0087) Detachment of the peptide from the ionic liquid based solid support via C-terminal approach (0088) The formed dipeptide, Leu-Gly was detached from the ionic liquid based solid support by treating with small amount of trifluoroacetic acid followed by triethylamine for 30 min to 4 h under stirring and/or shaking conditions inside the glass reactor. The obtained dipeptide was separated after washing and then qualitatively as well as quantitatively analyzed using a 1H NMR and HPLC analysis.
  • 71
  • [ 3303-31-9 ]
  • (3S,6S)-3,6-diisobutylpiperazine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 178.84 - 197.84℃; 2.4. Kinetic analysis of cyclization of Leu-Leu in solid state Kinetic analysis was performed following the ICTAC recommendations[52,53] using the NETZSCH Kinetics Neo 2.1.2.2 softwarepackage. The “model-free” Ozawa-Flynn-Wall (OFW) [54-56] andKissinger-Akahira-Sunose (KAS) Eq. (6) methods [57,58] were used.The same set of experimental data was used further for finding thetopochemical equation as described in Ref. [29-31,59]. A suitable kineticmodel was estimated using the following model-based approaches:reaction of nth order with autocatalysis by product (CnB) Eq.(7), reaction of nth order with m-Power autocatalysis by product (Cnm)Eq. (8), expanded Prout-Tompkins equation (Bna) Eq. (9).ln(β/T2) = Const - Ea/RT (6)d /dt = A exp(E /RT)(1 )n(1 + k )a cat (7)d /dt = A exp(E /RT)(1 )n(1 + k )catma (8)d /dt = A exp(E /RT)(1 )n ka cat (9) where β is heating rate, dα / dt - reaction rate, A - Arrhenius constant(pre-exponential factor), Ea - activation energy, R - gas constant, T -temperature, n - reaction order, kcat - catalytic rate constant, α -conversion degree (conversion rate), m - exponent.
  • 72
  • [ 3303-31-9 ]
  • C32H56N4O8 [ No CAS ]
  • C44H78N6O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: L-leucyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #2: C32H56N4O8 In dichloromethane at 0 - 20℃; for 120h; Boc-(L-Leu)2-L-SerOPte-(L-Leu)2-Ac5c-OMe (16) To a solution of Boc-protected peptide 14 (307 mg, 0.491mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (0.982 mL) dropwise at room temperature,and the reaction mixture was stirred overnight at the same temperature. The reaction mixture wasneutralized by adding sat. aq NaHCO3, and the aqueous phase was extracted with CHCl3 four times. The combined organic extracts were dried over anhydrous MgSO4 and concentrated under a vacuumto give crude product 15 (295 mg, quant), which was used for the next step without furtherpurification. Rf = 0.20 (60% EtOAc in n-hexane). To a solution of Boc-(L-Leu)2-OH (194 mg, 0.562mmol) in CH2Cl2 (2 mL) were added EDCI·HCl (108 mg, 0.562 mmol) and HOBt·H2O (103 mg, 0.674mmol) at 0 °C, and the solution was stirred for 30 min. Then, a solution of amine 15 (295 mg, 0.562mmol) in CH2Cl2 (2 mL) was added to the reaction mixture at the same temperature, and the resultantmixture was gradually warmed to room temperature. After stirring for 5 days, the CH2Cl2 wasremoved and the residue was diluted with EtOAc. The solution was washed successively with 1 Mof HCl, water, sat. aq NaHCO3, and brine. The organic layer was dried over anhydrous MgSO4 andconcentrated in vacuo to give a crude product, which was purified by flash column chromatographyon silica gel (60% EtOAc in n-hexane) to give 16 (300 mg, 63%) as a white solid. Rf = 0.30 (60% EtOAcin n-hexane). Mp 243-246 °C. [α]25D -43.2 (c 1.02, CHCl3). 1H NMR (500 MHz, CDCl3) δ: 7.41 (d, J = 4.4Hz, 1H), 7.30 (d, J = 6.6 Hz, 1H), 7.13 (d, J = 8.1 Hz, 1H), 7.02 (s, 1H), 6.84 (d, J = 3.7 Hz, 1H), 5.76 (ddt,J = 17.1, 10.3, 6.6 Hz, 1H), 5.05-4.92 (m, 2H), 5.00 (s, 1H), 4.42-4.34 (m, 1H), 4.34-4.27 (m, 1H), 4.25-4.20 (m, 1H), 4.06-3.96 (m, 2H), 3.86 (dd, J = 10.0, 5.4 Hz, 1H), 3.67 (s, 3H), 3.67-3.64 (m, 1H), 3.50-3.38(m, 2H), 2.27-2.00 (m, 6H), 1.87-1.51 (m, 18H), 1.48 (s, 9H), 1.02-0.83 (m, 24H). 13C NMR (125 MHz,CDCl3) δ: 174.9, 174.3, 173.4, 172.47, 172.45, 170.9, 156.6, 137.8, 114.9, 81.5, 70.5, 68.7, 65.7, 56.3, 54.3,54.0, 53.4, 52.2, 52.0, 40.2, 39.62 (2C), 39.59, 39.4, 37.2, 36.8, 30.1, 28.7, 28.22 (3C), 28.17 (2C), 25.0, 24.9,24.8, 24.7, 24.4, 24.3, 23.4, 22.9, 21.5, 21.2, 20.7. IR (KBr): 3277, 2957, 1719, 1630, 1560 cm-1. HRMS (ESI)m/z: [M + Na]+ calcd for C44H78N6O10Na, 873.5677; found, 873.5658.
  • 73
  • [ 85-44-9 ]
  • [ 3303-31-9 ]
  • [ 94683-09-7 ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine In toluene at 130℃; Dean-Stark;
  • 74
  • [ 85-44-9 ]
  • [ 3303-31-9 ]
  • (S)-N-((S)-5,5-dimethyl-2-oxotetrahydrofuran-3-yl)-2-(1,3-dioxoisoindolin-2-yl)-4-methylpentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / toluene / 130 °C / Dean-Stark 2: dihydrogen peroxide; C38H66N4Si2*2CF3O3S(1-)*Mn(2+); trifluorormethanesulfonic acid / water; 2,2,2-trifluoroethanol / 1 h / 0 - 25 °C
Same Skeleton Products
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