N-Carbobenzoxy-L-valine → (S)-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-cyclohexyl-acetic acid methyl ester

HRID 2242439Notes

Reaction equation

HRID 2242439 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@@H:4]([NH:11][C:12]([O:14]C(C)(C)C)=O)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[NH:20]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@H:21](C(O)=O)[CH:22]([CH3:24])[CH3:23].C(OC([C@@]1(NC([C@@H]2C[C@@H](OC3C4C(=CC(OC)=CC=4)N=C(C4C=CC=CC=4)C=3)C[C@H]2C(=O)N[C@H](C(=O)N[C@@H](C2CCCCC2)C(=O)NC)C(C)(C)C)=O)C[C@H]1C=C)=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C@@H:4]([NH:11][C:12](=[O:14])[C@@H:21]([NH:20][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH:22]([CH3:24])[CH3:23])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 726987N-Carbobenzoxy-L-valineHCID 13773589Boc-Chg-OmeHCID 59204178(1R,2S)-1-{[(1R,2R,4S)-2-{(S)-1-[((S)-Cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 57892932(S)-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-cyclohexyl-acetic acid methyl esterYield 94.4%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

Compound 54 (93 mg, 0.343 mmol) was deprotected and coupled to Z-Val-OH (95 mg, 0.378 mmol) according to the method for the preparation of 39. Flash column chromatography (toluene/ethyl acetate 4:1) gave 55 (131 mg, 94%) as a colorless solid.

Sources & evidence

ORD record
ord-81c14632339040ec9f9a0ab3920c25ed
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

Loading…