(2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid → HCID 70047483, compound

HRID 1647204Notes

Reaction equation

HRID 1647204 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C@@H:21]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:22]([OH:37])[CH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[C:30]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:20][C@@H:21]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C@H:22]([OH:37])[CH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[C:30]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:19])[C:13]([CH3:14])([CH3:15])[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 9899995(2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acidHCID 70049550HCID 70049550, compound

Product 1

HCID 70047483HCID 70047483, compoundYield 25.9%

Procedure

In a manner analogous to that described in Example 6, 68 mg (0.26 mmol) of N-benzyloxycarbonyl-3-methyl-L-valine were coupled with 90 mg (0.26 mmol) of 2(S)-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide to give 40 mg of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-3-methyl-L-valyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide as a white solid of melting point 90° C. (decomposition); MS m/e 594 [M+H]+.

Sources & evidence

ORD record
ord-d967ca30f2b84c6da554afb9a62f7921
Source dataset
uspto-grants-1995_07
Patent number
US05430041

Reaction notes

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