N-Carbobenzoxy-L-valine → HCID 70049680, compound

HRID 1647200Notes

Reaction equation

HRID 1647200 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C@@H:20]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:21]([OH:36])[CH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[C:29]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([NH:19][C@@H:20]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C@H:21]([OH:36])[CH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[C:29]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:18])[CH:13]([CH3:14])[CH3:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 726987N-Carbobenzoxy-L-valineHCID 70049550HCID 70049550, compound

Product 1

HCID 70049680HCID 70049680, compoundYield 47.6%

Procedure

In a manner analogous to that described in Example 6, 73 mg (0.29 mmol) of N-benzyloxycarbonyl-L-valine were coupled with 100 mg (0.29 mmol) of 2(S)-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide to give 80 mg of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-valyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide as a white solid; MS m/e 580 [M+H]+.

Sources & evidence

ORD record
ord-2c8bd0d0024b45c3b0e23f244b0fddd1
Source dataset
uspto-grants-1995_07
Patent number
US05430041

Reaction notes

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