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[ CAS No. 6234-01-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6234-01-1
Chemical Structure| 6234-01-1
Structure of 6234-01-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6234-01-1 ]

CAS No. :6234-01-1 MDL No. :MFCD00153438
Formula : C10H20ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :YIFPACFSZQWAQF-FJXQXJEOSA-N
M.W : 253.72 Pubchem ID :16218751
Synonyms :
H-Glu(OtBu)-OMe.HCl
Chemical Name :H-Glu(OtBu)-OMe.HCl

Calculated chemistry of [ 6234-01-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.46
TPSA : 78.62 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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.21
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 0.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 4.91 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (Ali) : -2.46
Solubility : 0.884 mg/ml ; 0.00348 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.36
Solubility : 11.0 mg/ml ; 0.0434 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.63

Safety of [ 6234-01-1 ]

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 [ 6234-01-1 ]

* 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 [ 6234-01-1 ]

[ 6234-01-1 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 1070-19-5 ]
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  • [ 18635-51-3 ]
  • 2
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  • [ 38155-01-0 ]
  • 3
  • [ 64-17-5 ]
  • [ 6234-01-1 ]
  • [ 112408-16-9 ]
  • 4
  • [ 2389-60-8 ]
  • [ 6234-01-1 ]
  • [ 38155-01-0 ]
  • 5
  • [ 25474-85-5 ]
  • [ 6234-01-1 ]
  • p-Methoxycarbobenzoxy-Glu-α-OMe-γ-OBut [ No CAS ]
  • 6
  • [ 6234-01-1 ]
  • [ 3967-21-3 ]
  • [ 35793-59-0 ]
  • 7
  • [ 6234-01-1 ]
  • benzyloxycarbonyl-D-glutamic acid γ-t-butyl ester dicyclohexylammonium salt [ No CAS ]
  • [ 35793-61-4 ]
  • 8
  • [ 674-82-8 ]
  • [ 6234-01-1 ]
  • [ 113744-02-8 ]
  • 9
  • [ 2942-58-7 ]
  • [ 19741-14-1 ]
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  • [ 79640-68-9 ]
  • [ 95485-10-2 ]
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  • 10
  • [ 19741-14-1 ]
  • [ 6234-01-1 ]
  • [ 79640-68-9 ]
  • [ 95485-10-2 ]
  • [ 95485-11-3 ]
  • 11
  • [ 6234-01-1 ]
  • C20H21N7O5 [ No CAS ]
  • [ 95484-99-4 ]
  • 12
  • [ 6234-01-1 ]
  • [ 95063-86-8 ]
  • [ 95485-07-7 ]
  • 13
  • [ 6234-01-1 ]
  • [ 122-04-3 ]
  • [ 95485-03-3 ]
  • 14
  • [ 6234-01-1 ]
  • [ 610-14-0 ]
  • [ 112113-83-4 ]
  • 15
  • [ 6234-01-1 ]
  • [ 100-39-0 ]
  • [ 635-21-2 ]
  • 3-((S)-1-Benzyl-7-chloro-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-yl)-propionic acid [ No CAS ]
  • 16
  • [ 6234-01-1 ]
  • [ 170787-77-6 ]
  • [ 328236-10-8 ]
  • 17
  • [ 6234-01-1 ]
  • (R)-2-[(S)-2-((R)-2-{(S)-2-[3-(3,5-Dimethyl-phenyl)-ureido]-3-phenyl-propionylamino}-4-methyl-pentanoylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid [ No CAS ]
  • 3',5'-dimethylphenyl-ureido-(Phe-D-Leu)2-Glu-(OtBu)-OMe [ No CAS ]
  • 18
  • [ 6234-01-1 ]
  • [ 1694-92-4 ]
  • [ 856865-57-1 ]
  • 19
  • [ 10541-83-0 ]
  • [ 6234-01-1 ]
  • [ 95485-08-8 ]
  • 20
  • [ 6234-01-1 ]
  • [ 913625-16-8 ]
  • 21
  • [ 6234-01-1 ]
  • [ 913625-15-7 ]
  • 22
  • [ 6234-01-1 ]
  • 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[6-(6-fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester [ No CAS ]
  • 23
  • [ 6234-01-1 ]
  • 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-(5-{2-[6-(6-fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-pentylcarbamoyl)-butyric acid [ No CAS ]
  • 24
  • [ 6234-01-1 ]
  • [ 913625-20-4 ]
  • 25
  • [ 6234-01-1 ]
  • [ 913625-19-1 ]
  • 26
  • [ 6234-01-1 ]
  • [ 913625-18-0 ]
  • 27
  • [ 6234-01-1 ]
  • [ 913625-17-9 ]
  • 29
  • [ 6234-01-1 ]
  • [ 66147-29-3 ]
  • 30
  • [ 6234-01-1 ]
  • [ 856865-72-0 ]
  • 31
  • [ 6234-01-1 ]
  • [ 856865-94-6 ]
  • 32
  • [ 6234-01-1 ]
  • (S)-2-{(S)-4-tert-Butoxycarbonyl-2-[methyl-(2-nitro-benzenesulfonyl)-amino]-butyrylamino}-4-methyl-pentanoic acid [ No CAS ]
  • 33
  • [ 6234-01-1 ]
  • 1-[4-(((3,5-dimethylanilino)carbonyl)methyl)phenoxy]cyclopentanecarbonyl-L-glutamate [ No CAS ]
  • 34
  • [ 6234-01-1 ]
  • [ 112113-77-6 ]
  • 35
  • [ 6234-01-1 ]
  • [ 112113-84-5 ]
  • 37
  • [ 6234-01-1 ]
  • [ 95485-02-2 ]
  • 38
  • [ 6234-01-1 ]
  • [ 95485-04-4 ]
  • 39
  • [ 6234-01-1 ]
  • [ 95484-98-3 ]
  • 40
  • [ 6234-01-1 ]
  • [ 95485-12-4 ]
  • 41
  • [ 6234-01-1 ]
  • [ 95485-13-5 ]
  • 42
  • [ 6234-01-1 ]
  • [ 95485-05-5 ]
  • 43
  • [ 6234-01-1 ]
  • [ 95485-08-8 ]
  • 47
  • [ 6234-01-1 ]
  • Z-Lys(Boc)-Glu(OtBu)-NHNH2 [ No CAS ]
  • 48
  • [ 6234-01-1 ]
  • (S)-2-((S)-2-Amino-4-tert-butoxycarbonyl-butyrylamino)-pentanedioic acid 5-tert-butyl ester 1-methyl ester [ No CAS ]
  • 50
  • [ 6234-01-1 ]
  • p-Methoxy-(-)-carbobenzoxy-Glu-γ-OBut [ No CAS ]
  • 51
  • [ 6234-01-1 ]
  • [ 220302-42-1 ]
YieldReaction ConditionsOperation in experiment
With LiOH; In tetrahydrofuran; water; Example 21 Synthesis of N-(Toluene-4-sulfonyl)-L-prolyl-L-glutamic acid N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to L-5-(1,1-dimethylethyl)-glutamic acid methyl ester hydrochloride using the procedure described in Method 3. The methyl ester was hydrolyzed using LiOH in THF/water to provide a solid, mp=164-166 C. The title compound was prepared, via cleavage of the t-butyl ester using trifluoroacetic acid in CH2Cl2, as a solid, mp=>200 C.
  • 52
  • [ 1149-26-4 ]
  • [ 6234-01-1 ]
  • [ 543-27-1 ]
  • N-Benzyloxycarbonyl-L-valyl-γ-t-butyl-L-glutamic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
168.5 g (78%) With 4-methyl-morpholine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; (a) N-Benzyloxycarbonyl-L-valyl-gamma-t-butyl-L-glutamic acid methyl ester N-Benzyloxycarbonyl-L-valine (144 g, 0.58 mol, 1.2 eq) was dissolved in 400 ml freshly distilled THF and stirred mechanically in a 3-l 3-neck round bottom flask fitted with a thermometer and dropping funnel and immersed in a dry ice-alcohol bath at -15. While stirring at -15, N-methylmorpholine (55 ml, 0.58 mol, 1.2 eq) was added dropwise. The temperature was maintained at -15 and isobutylchloroformate (66.2 ml, 0.58 mol, 1.2 eq) was added dropwise over a 2 min period. The reaction mixture stirred for an additional 2 min at -15 and a precooled (-20) solution of L-glutamic acid alpha-methyl ester gamma-t-butyl ester.HCL (120.8 g, 0.48 mol) dissolved in 300 ml THF and 150 ml DMF was added dropwise with simultaneous addition of N-methylmorpholine (46 ml, 0.48 mol). [The addition took 6 min while maintaining the temperature below -15.] The reaction mixture was stirred for 30 min at -15, and for 3 h at 25, evaporated in vacuo and the residue dissolved in EtOAc (900 ml) and washed with 10% NaHCO3 (3*200 ml), 1M citric acid (3*200 ml) and satd. NaCl solution (1*200 ml). The aqueous washes were backwashed with EtOAc and the combined organic layers were dried over MgSO4, filtered and concentrated to ~200 ml and pet. ether (1 l) added. The solid was collected and dried in vacuo(*) and the combined crops were recrystallized from CCl4 (400 ml) pet. ether (1.2 l) to yield 168.5 g (78%) of white crystalline product; mp 66.5-68; Rf 0.74 (n-BuOH:AcOH:EtOAc:H2 O; 1-1-1-1),Rf 0.73 (CHCl3:CH3 OH:AcOH; 80-5-1); [alpha]D25 -28.91, (c 1, MeOH). Anal. calc. for C23 H24 N2 O7 (450.5): C, 61.32; H, 7.61; N, 6.22. Found: C, 61.23; H, 7.58; N, 6.01.
  • 53
  • 2-(S)allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionic acid hydrochloride [ No CAS ]
  • [ 6234-01-1 ]
  • 2-(S)-[2-(S)-allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.8 g (50%) With N-ethylmorpholine;; In ethyl acetate; N,N-dimethyl-formamide; 2-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride To 2-(S)allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionic acid hydrochloride (3.48 g, 10.6 mmol) and 2-(S)-amino-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride (2.7 g, 10.6 mmol) in 20 ml of DMF were added at -15 C. TOTU (3.83 g, 11.67 mmol) and N-ethylmorpholine (2.7 ml, 21.2 mmol). The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation, ethyl acetate was added to the residue and the organic layer was extracted with aqueous sodium hydrogen carbonate solution, potassium hydrogen sulfate solution, and water. The organic layer was evaporated. Yield: 2.8 g (50%). MS: m/z=491.3 (M+H)+.
  • 54
  • 5-hydroxy-1-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]
  • [ 6234-01-1 ]
  • [ 1164338-16-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In dichloromethane; at 20℃; for 16h;Product distribution / selectivity; Example 99: (S)-4-[5-(3,3-Dimethyl-2-oxo-butoxy)-1 -phenyl-1 H-pyrazole-3-carbonyl]- amino}-5-oxo-5-[4-(2-oxo-2-pyrrolidin-1 -yl-ethyl)-piperazin-1 -yl]-pentanoic acid; (i) (S)-2-[(5-Hydroxy-1 -phenyl-1 H-pyrazole-3-carbonyl)-amino]-pentanedioic acid 5- tert-butyl ester 1 -methyl ester; To a solution of 8 g of 5-Hydroxy-1 -phenyl-1 H-pyrazole-3-carboxylic acid and 10 g of(S)-2-Amino-pentanedioic acid 5-tert-butyl ester 1 -methyl ester hydrochloride in 300 ml of DCM, 16 g of triethylamine and 15 g of HATU was added and strirred for 16 h at RT. Then, the reaction mixture was diluted with water and extracted with DCM. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n- heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 11 g.
  • 55
  • [ 1163792-11-7 ]
  • [ 6234-01-1 ]
  • [ 1163792-41-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 24h; Example 103: (S)-5-[4-(3-Chloro-benzoyl)-piperidin-1 -yl]-4-({5-[2-((S)-2- cyclobutylcarbamoyl-pyrrolidin-1 -yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}- amino)-5-oxo-pentanoic acid; i) (S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1 -yl)-2-oxo-ethoxy]-1 -phenyl-1 H- pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester 1 -methyl ester; To a solution of 1.1 g 5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1- phenyl-1 H-pyrazole-3-carboxylic acid in 20 ml DMF were added 1 ml DIPEA, 0.41 g HOBt, 0.51 g EDC and 0.68 g H-GIu(OtBu)-OMe hydrochloride. After stirring for 24 h the solution was concentrated, taken up with dichloromethane and subsequently extracted with aqueous LiCI (4 %), 0.1 M HCI and saturated NaHCO3. The crude product was purified by flash chromatography on silica using an ethyl acetate/heptane 50:50 to 100:0 gradient. Yield: 1.88 g colorless foam.
  • 56
  • [ 23519-90-6 ]
  • [ 6234-01-1 ]
  • [ 1239168-35-4 ]
  • 57
  • [ 6234-01-1 ]
  • [ 1268620-20-7 ]
  • 58
  • [ 6234-01-1 ]
  • [ 1268620-21-8 ]
  • 59
  • [ 6234-01-1 ]
  • [ 1268620-22-9 ]
  • 60
  • [ 1268620-24-1 ]
  • [ 6234-01-1 ]
  • [ 1268620-23-0 ]
YieldReaction ConditionsOperation in experiment
52% Example 46 (S)-5-tert-butyl 1-methyl 2-[(5-{4-[3-fluoro-4-([(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}pentanedioate A mixture of 5-{4-[3-fluoro-4-([(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxylic acid (500 mg, 1.1 mmol), HATU (500 mg, 1.32 mmol) and N,N-diisopropylethylamine (426 mg, 3.3 mmol) in anhydrous DMF (8 ml) was stirred at room temperature for 10 minutes, followed by addition of L-Glutamic acid 5-tert-butyl 1-methyl ester hydrochloride (334 mg, 1.32 mmol). The mixture was stirred for another 10 minutes and poured into 200 ml of water. 2M HCl was added dropwise until pH=5. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluding with 3-5% MeOH/CHCl3 to give (S)-5-tert-butyl 1-methyl 2-[(5-{4-[3-fluoro-4-([(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}pentanedioate as off-white solid. Yield: 380 mg, 52%. 1H NMR (DMSO-d6) delta: 11.87 (br. s., 1H), 8.96 (s, 1H), 8.56 (br. s., 1H), 8.38 (d, J=5.6 Hz, 1H), 8.20 (t, J=8.9 Hz, 1H), 8.08 (d, J=7.0 Hz, 1H), 7.44 (br. s., 1H), 7.23-7.29 (m, 2H), 7.18-7.23 (m, 2H), 7.11-7.17 (m, 2H), 7.01 (d, J=8.8 Hz, 1H), 6.79 (d, J=7.0 Hz, 1H), 6.70-6.76 (m, 1H), 4.32-4.41 (m, 1H), 3.60 (s, 3H), 2.23-2.31 (m, 5H), 1.93-2.03 (m, 1H), 1.81-1.91 (m, 1H), 1.35 (s, 9H) LR MS (ES+): 646 (MH), 668 (M+Na+) LR MS (ES-): 644 (M-H)
52% Example 46(S)-5-tert-butyl 1-methyl 2-[(5-{4-[3-fluoro-4-([(3- methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3- yl)carbonyl]amino}pentanedioateA mixture of 5-{4-[3-fluoro-4-([(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxylic acid (500mg, 1.1mmol), HATU (500mg, 1.32mmol) and N,N- diisopropylethylamine (426mg, 3.3mmol) in anhydrous DMF (8ml) was stirred at room temperature for 10 minutes, followed by addition of L-Glutamic acid 5-tert-butyl 1-methyl ester hydrochloride (334mg, 1.32mmol). The mixture was stirred for another 10 minutes and poured into 200ml of water. 2M HCl was added dropwise until pH = 5. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 3~5% MeOH/CHCl3 to give (S)-5-tert-butyl 1-methyl 2-[(5-{4- [3-fluoro-4-([(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3- yl)carbonyl]amino}pentanedioate as off-white solid. Yield: 380mg, 52%. 1H NMR (DMSO-d6): 11.87 (br. s., 1H), 8.96 (s, 1H), 8.56 (br. s., 1H), 8.38 (d, J = 5.6 Hz, 1H), 8.20 (t, J = 8.9 Hz, 1 H), 8.08 (d, J = 7.0 Hz, 1H), 7.44 (br. s., 1H), 7.23 - 7.29 (m, 2H), 7.18 - 7.23 (m, 2H), 7.11 - 7.17 (m, 2H), 7.01 (d, J = 8.8 Hz, 1H), 6.79 (d, J = 7.0 Hz, 1H), 6.70 - 6.76 (m, 1H), 4.32 - 4.41 (m, 1H), 3.60 (s, 3H), 2.23 - 2.31 (m, 5H), 1.93 - 2.03 (m, 1H), 1.81 - 1.91 (m, 1H), 1.35 (s, 9H) LR MS (ES+): 646 (MH), 668 (M+Na+) LR MS (ES-): 644 (M-H)
  • 61
  • [ 6234-01-1 ]
  • [ 1162070-13-4 ]
  • 62
  • [ 6234-01-1 ]
  • [ 1356964-21-0 ]
  • 63
  • [ 6234-01-1 ]
  • [ 1356964-22-1 ]
  • 64
  • [ 252847-30-6 ]
  • [ 6234-01-1 ]
  • [ 1162070-20-3 ]
YieldReaction ConditionsOperation in experiment
Example 1(S)-5-tert-butyl 1-methyl 2-(4-(2,2,2-trifluoro-N-((2-isobutyramido-4-oxo-3,4-dihydropteridin-6-yl)methyl)acetamido)benzamido)pentanedioate A solution of 1a (0.20 g, 0.41 mMol) in anhydrous DMF (1.7 mL) was treated with HBTU (0.158 g, 0.41 mMol), followed by diisopropylethylamine (0.08 mL, 2.01 mMol) under an atmosphere of anhydrous nitrogen, at room temperature, for 20 minutes. A solution of L-glutamic acid gamma-t-butyl ester alpha-methyl; ester hydrochloride (0.10 g, 0.41 mMol) in DMF (0.5 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured onto 200 g ice and stirred rapidly until the ice melted. The solids were collected by filtration and washed with pentane. Further drying under high vacuum (0.1 mmHg, room temperature, 24 hours) gave 2a as an orange solid (0.28 g). MS (AP+) 700.6 (M+Na). MS (AP-) 676.7 (M-1).
  • 65
  • [ 6234-01-1 ]
  • (S)-4-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)-5-methoxy-5-oxopentanoic acid [ No CAS ]
  • 66
  • [ 6234-01-1 ]
  • (S)-methyl 18-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)-2,2-dimethyl-4,15-dioxo-3,8,11-trioxa-5,14-diazanonadecan-19-oate [ No CAS ]
  • 67
  • [ 6234-01-1 ]
  • (S)-2-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)-5-(2-(2-(2-aminoethoxy)ethoxy)ethylamino)-5-oxopentanoic acid [ No CAS ]
  • 68
  • pteroic acid dihydrochloride [ No CAS ]
  • [ 6234-01-1 ]
  • (S)-5-tert-butyl 1-methyl 2-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)pentanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; To pteroic acid dihydrochloride (100 mg, 0.26 mmol), triethylamine (1.5 mL, 11 mmol), and <strong>[6234-01-1](S)-5-tert-butyl 1-methyl 2-aminopentanedioate hydrochloride</strong> (162 mg, 0.64 mmol) in N,N-dimethylformamide (3 mL), 2-(2-pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (190 mg, 0.64 mmol) was added in one portion. The reaction was stirred at ambient temperature for 16 hours. After this time, the reaction was purified by semi-preparative HPLC (1:4 to 0:100 H2O/CH3CN over 25 minutes) to afford(S)-5-tert-butyl 1-methyl 2-(4-((2-amino-4-hydroxypteridin-6-yl)methylamino)benzamido)pentanedioate (55 mg, 34%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 8.56 (s, 1H), 8.26 (d, J=6.6 Hz, 1H), 7.65 (d, J=8.0 Hz, 2H), 6.94 (bs, 4H), 6.65 (d, J=8.0 Hz, 2H), 4.58-4.34 (m, 3H), 3.61 (s, 3H), 2.36-2.25 (m, 2H), 2.10-1.88 (m, 2H), 1.37 (s, 9H); MM-APCI MS m/z=510 [M-H]-.
  • 69
  • [ 6234-01-1 ]
  • 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoic acid [ No CAS ]
  • 70
  • [ 6234-01-1 ]
  • tert-butyl 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoate [ No CAS ]
  • 71
  • [ 1268619-84-6 ]
  • [ 6234-01-1 ]
  • 5-tert-butoxy-2-[({5-[4-(2-fluoro-5-[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Example 2575-tert-butoxy-2-[({5-[4-(2-fluoro-5-[(2-fluoro-5- methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5- oxopentanoic acidTo a stirred solution of 5-[4-(2-fluoro-5-[(2-fluoro-5- methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid (150mg, 0.33mmol) in 10ml of anhydrous DMF were added HATU (150mg, 0.39mmol) and N,N- diisopropylethylamine (128mg, 0.99mmol). The mixture was stirred at room temperature for 10 minutes, followed by addition of L-Glutamic acid 5-tert-butyl ester (102mg, 0.50mmol). The mixture was heated at 60C for 30 minutes, cooled to room temperature, and poured into 100ml of water. 2M HCl was added dropwise with vigorous stirring until pH = 4. The precipitates were filtered, washed with water and dried in vacuo to give 5-tert-butoxy-2-[({5-[4-(2-fluoro-5- [(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3- yl}carbonyl)amino]-5-oxopentanoic acid as white solid. Yield: 185mg, 87%. 1H NMR (DMSO-d6): 12.49 (br. s., 1H), 11.88 (br. s., 1H), 10.12 (s, 1 H), 8.42 (d, J = 5.9 Hz, 1H), 7.96 - 8.02 (m, 2H), 7.95 (d, J = 7.9 Hz, 1H), 7.63 (dd, J = 10.1, 8.7 Hz, 1H), 7.46 (dd, J = 3.1, 1.6 Hz, 1H), 7.34 (dd, J = 7.3, 1.8 Hz, 1H), 7.29 (d, J = 2.6 Hz, 1H), 7.19 (dd, J = 2.6, 1.8 Hz, 1H), 7.14 (dd, J = 10.4, 8.4 Hz, 1H), 7.02 - 7.06 (m, 1H), 6.80 (dd, J = 5.6, 2.3 Hz, 1H), 4.32 (ddd, 1H), 2.28 (t, J = 7.9 Hz, 2H), 2.26 (s, 3H), 1.94 - 2.04 (m, 1H), 1.80 - 1.89 (m, 1H), 1.36 (s, 9H) LR MS (ES-): 633 (M-H)
  • 72
  • [ 1268619-96-0 ]
  • [ 6234-01-1 ]
  • 5-tert-butyl 1-methyl 2-([5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)pentanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Example 2675-tert-butyl 1-methyl 2-([5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol- 3-yl]carbonyl}amino)pentanedioateTo a stirred solution of 5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3- carboxylic acid (Example 32)(140mg, 0.35mmol) in 10ml of anhydrous DMF were added HATU (160mg, 0.42mmol) and N,N-diisopropylethylamine (135mg, 1.05mmol). The mixture was stirred at room temperature for 10 minutes, followed by addition of L-Glutamic acid 5-tert- butyl 1-methyl ester hydrochloride (135mg, 0.53mmol). The mixture was stirred for another 5 minutes and poured into 100ml of water. 2M HCl was added dropwise with vigorous stirring until pH = 4. The precipitates were filtered, washed with water and dried in vacuo to give 5-tert- butyl 1-methyl 2-([5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3- yl]carbonyl}amino)pentanedioate as white solid. Yield: 170mg, 81%. 1H NMR (DMSO-d6): 11.96 (br. s., 1H), 10.21 (s, 1H), 8.42 (d, J = 5.9 Hz, 1H), 8.10 (d, J = 7.6 Hz, 1H), 7.77 (d, J = 1.5 Hz, 1H), 7.68 - 7.72 (m, 2H), 7.48 (br. s., 1H), 7.42 (t, J = 8.4 Hz, 1H), 7.29 (br. s., 1H), 7.19 (br. s., 1H), 6.91 (dd, J = 7.6, 1.8 Hz, 1H), 6.80 (br. s., 1H), 6.56 (d, J = 1.2 Hz, 1H), 4.37 (ddd, J = 9.5, 7.5, 5.3 Hz, 1H), 3.60 (s, 3H), 2.29 (s, 3H), 2.28 (t, J = 7.6 Hz, 2H), 1.94 - 2.02 (m, 1H), 1.82 - 1.91 (m, 1H), 1.35 (s, 9H) LR MS (ES+): 625 (M+Na+) LR MS (ES-): 601 (M-H)
  • 73
  • [ 3160-59-6 ]
  • [ 6234-01-1 ]
  • C24H36N2O7 [ No CAS ]
  • 74
  • [ 3160-59-6 ]
  • [ 6234-01-1 ]
  • C16H30N2O5 [ No CAS ]
  • 75
  • [ 37793-53-6 ]
  • [ 6234-01-1 ]
  • (S)-5-tert-butyl 1-methyl 2-(4-{N-[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]-2,2,2-trifluoroacetamido}benzamido)pentanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% HCl-H2N-Glu(OtBu)-OMe (350 mg, 1.38 mmol) was added to a solution of N10-TFA-Pteroic Acid (560 mg, 1.37 mmol) and DIPEA (1.2 rriL, 6.85 mmol) in DMSO (6.0 rriL) at 23 C under N2. After stirring for 15 min at 23 C, PyBOP (720 mg, 1.0 mmol) was added, and the reaction mixture was stirred for 24 h at 23 C. Volatile material was removed under reduced vacuum to afford the crude product as a semi-solid, which was further purified via solid extraction with Hex/EA (1/1) 3 times to provide QC02023 as a pale-yellow solid in quantitative yield, which was used without further purification
  • 76
  • [ 6234-01-1 ]
  • (S)-4-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-5-methoxy-5-oxopentanoic acid [ No CAS ]
  • 77
  • [ 6234-01-1 ]
  • (S)-methyl 18-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-2,2-dimethyl-4,15-dioxo-3,8,11-trioxa-5,14-diazanonadecan-19-oate [ No CAS ]
  • 78
  • [ 6234-01-1 ]
  • (S)-methyl 2-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-5-((2-(2-(2-aminoethoxy)ethoxy)ethyl)amino)-5-oxopentanoate [ No CAS ]
  • 79
  • [ 6234-01-1 ]
  • (S)-2,2'-(7-(4-(4-(N-((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)-2,2,2-trifluoroacetamido)benzamido)-3,7,18-trioxo-2,11,14-trioxa-8,17-diazanonadecan-19-yl)-1,4,7-triazonane-1,4-diyl)diacetic acid [ No CAS ]
  • 80
  • [ 6234-01-1 ]
  • (S)-2,2'-(7-(1-(4-(((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)phenyl)-3-carboxy-1,6,17-trioxo-10,13-dioxa-2,7,16-triazaoctadecan-18-yl)-1,4,7-triazonane-1,4-diyl)diacetic acid [ No CAS ]
  • 81
  • [ 6234-01-1 ]
  • [ 75932-02-4 ]
  • Fmoc-L-Lys(Fmoc)-L-Glu(OtBu)-OMe [ No CAS ]
  • 82
  • [ 6234-01-1 ]
  • C39H45F3N11O9(1+)*CF3O3S(1-) [ No CAS ]
  • 83
  • [ 6234-01-1 ]
  • C33H35FN10O8 [ No CAS ]
  • 84
  • [ 6234-01-1 ]
  • [ 462100-44-3 ]
  • H-(N<SUP>2</SUP>-Boc)aGlu(tBu)-OMe [ No CAS ]
  • 85
  • [ 121-66-4 ]
  • [ 32315-10-9 ]
  • [ 6234-01-1 ]
  • C14H20N4O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% General procedure: A solution of triphosgene (0.4 mmol) in dry CH2C12 (2.5 mL) was prepared underargon atmosphere in a dry round bottom flask and cooled to 0 C. A solution of amine (1.0 mmol) and triethylamine (2.2 - 3.2 mmol) in dry CH2C12 (1.9 mL) which wasprepared under argon atmosphere in a dry round bottom flask was added dropwise to the first solution. The ice bath was removed after 15 minutes and the reaction mixture was stilTed for 1 h at room temperature. In another round bottom flask under argon, triethylamine (1.1 mmol) was added to a solution of thiazole (1.1 mmol) in dry DMF (1.3 mL). This solution was cooled to 0C and the isocyanate solution was added. The redreaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel column (CH2C12/MeOH 10:0 to 95:5 (v/v) in 30 mm) to afford an oil or a solid, which was triturated in hexanes and CH2C12 and filtered to afford the ureaObtained according general procedure A from <strong>[6234-01-1]glutamic acid 5-tert-butyl 1-methyl ester hydrochloride</strong> and 2-amino-5-nitrothiazole. Yellow solid (0.221 g, 36%). MS (ESI-): m/z = 387 [M-H1. To a solution (EtOH/THF 2/1, 1.0 mL) of the previously prepared urea (0.221 g, 0.57 mmol, 1.0 eq.) at 0C was added 1M lithium hydroxideaqueous solution (0.63 mL, 0.026 g, 0.63 mmol, 1.1 eq.). The mixture was stirred for 16 h at room temperature and 60 h at 50 C. The reaction mixture was diluted in CH2C12 and H20. The organic phase was discarded and the aqueous layer was acidified with 1 N hydrochloric acid solution until pH 1 and extracted three times with CH2C12. The combined organic layers were dried over Na2504 and concentrated under reducedpressure to give an orange oil (0.119 g). This oil was precipitated in CH2C12 and solid was filtered affording the monoacid as a white powder (0.03 2 g, 15 %). MS (ESI-): mlz = 373 [M-H1. 1H NMR (DMSO-d6) oe (ppm): 11.54 (br s, 0.5H), 8.53 (s, 1H), 7.20 (d, 1H, J = 7.6 Hz), 4.32-4.28 (m, 1H), 2.30-2.27 (m, 2H), 2.10-2.05 (m, 1H), 1.91-1.84 (m, 1H), 1.40 (s, 9H). The previous prepared monoacid (0.015 g, 0.04 mmol, 1 eq.) wassolubilized in CH2C12 (0.08 mL) and TFA (0.08 mL) at 0 C. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was dissolved in Et20 and was evaporated to dryness. This step was done three times affording the urea as a white solid (0.013 g, quantitative yield). Purity = 96%; tr = 0.80 mm; MS (ESI+): m/z = 319 [M+H1 HRMS mlz calculated for C9H11N4075 [M+H1 319.0343, found 319.0331. 1HNMR (DMSO-d6) oe (ppm): 11.54 (br s, 1H), 8.53 (s, 1H), 7.20 (d, 1H, J = 7.5 Hz), 4.30(d, 1H, J = 5.0 Hz), 2.35-2.24 (m, 2H), 2.12-2.05 (m, 1H), 1.92-1.85 (m, 1H). 13C NMR (DMSO-d6) oe (ppm): 173.5, 172.7, 163.8, 153.1, 143.2, 141.1, 52.1, 29.7, 26.7.
  • 86
  • [ 112-85-6 ]
  • [ 6234-01-1 ]
  • N-docosanoyl-L-glutamic acid 5-tert-butyl-1-methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 22h;Cooling with ice; To L-glutamic acid 5-tert-butyl-l-methyl ester (0992) hydrochloride (543 mg, 2.14 mmol) were added N,N- dimethylformamide (14.3 ml), and behenic acid (875 mg, 2.57 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (493 mg, 2.57 mmol), 1-hydroxybenzotriazole (347 mg, 2.57 mmol), and triethylamine (0.60 ml, 4.3 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 22 hr. Ethyl acetate (25 ml) was added and the mixture was filtered. The solid collected by filtration was washed three times with ethyl acetate (10 ml) and three times with methanol (10 ml) to give N-docosanoyl-L- glutamic acid 5-tert-butyl-l-methyl ester (281 mg, 0.52 mmol, yield 24%) as a white solid. (0993) 1H-NMR (400 MHz, CDC13)5: 0.88 (t, 3H, J=7.0 Hz), 1.25-1.28 (m, 36H) , 1.44(s, 9H), 1.62(m, 2H) , 1.96(m, 1H) , 2.12(m, 1H) , (0994) 2.20(t, 2H, J=7.6 Hz), 2.30(m, 2H) , 3.74(s, 3H) , 4.59 (dt, 1H, J=5.2 Hz, 8.0 Hz), 6.19(d, 1H, J=7.6 Hz). (0995) ESIMS(m/z): 540.5 ( [M+H] +) , 1079.9 ( [2 M+H] +) .
  • 87
  • [ 112-85-6 ]
  • [ 6234-01-1 ]
  • N-docosanoyl-L-glutamic acid 1-methyl ester [ No CAS ]
  • 88
  • [ 6234-01-1 ]
  • [ 57-10-3 ]
  • N-hexadecanoyl-L-glutamic acid 5-tert-butyl-1-methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 22h;Cooling with ice; To L-glutamic acid 5-tert-butyl-l-methyl ester (1079) hydrochloride (132 mg, 0.52 mmol) were added N,N- dimethylformamide (5.2 ml), and palmitic acid (200 mg, 0.78 mmol) at room temperature, and the mixture was cooled in an ice bath. Then, l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (150 mg, 0.78 mmol), 1-hydroxybenzotriazole (105 mg, 0.78 mmol), and triethylamine (0.22 ml, 1.56 mmol) were added, and the mixture was removed from the ice bath and stirred at room temperature for 22 hr. Silica gel was added to the reaction solution to evaporate the solvent, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give N-hexadecanoyl-L-glutamic acid 5-tert-butyl-l- methyl ester (214 mg, 0.47 mmol, yield 90%) as a white solid. FontWeight="Bold" FontSize="10" H-NMR (400 MHz, CDC13)5: 0.88 (t, 3H, J=6.8 Hz), 1.25-1.29 (m, 24H) , 1.44(s, 9H) , 1.63(m, 2H) , 1.95(m, 1H) , 2.13 (m, 1H) , (1080) 2.21(t, 2H, J=8.0 Hz), 2.31(m, 2H) , 3.75(s, 3H) , 4.60(dt, 1H, J=5.2 Hz, 8.0 Hz), 6.17(d, 1H, J=7.6 Hz). ESIMS(m/z): 456.4 ( [M+H] +) , 911.8 ( [2 M+H] +) .
  • 89
  • [ 6234-01-1 ]
  • [ 57-10-3 ]
  • [ 73793-91-6 ]
  • 90
  • [ 24424-99-5 ]
  • [ 6234-01-1 ]
  • [ 18635-51-3 ]
  • 91
  • [ 24424-99-5 ]
  • [ 6234-01-1 ]
  • Boc-L-Glu(O-t-Bu)-L-Ala-O-t-Bu [ No CAS ]
  • 92
  • [ 6234-01-1 ]
  • 1-methyl 5-(tert-butyl) N-((allyloxy)carbonyl)-N-hydroxy-L-glutamate [ No CAS ]
  • 93
  • [ 6234-01-1 ]
  • methyl-(S)-2-(((allyloxy)carbonyl)(hydroxy)amino)-5-hydroxypentanoate [ No CAS ]
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[ 6234-01-1 ]

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