Benzyloxycarbonyl-L-phenylalanine → HCID 70047624, compound

HRID 1647201Notes

Reaction equation

HRID 1647201 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C@@H:24]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:25]([OH:40])[CH2:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:23][C@@H:24]([CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C@H:25]([OH:40])[CH2:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 70049550HCID 70049550, compound

Product 1

HCID 70047624HCID 70047624, compoundYield 44.1%

Procedure

In a manner analogous to that described in Example 6, 78 mg (0.26 mmol) of N-benzyloxycarbonyl-L-phenylalanine 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 72 mg of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-phenylalanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide as a while solid; MS m/e 628 [M+H]+.

Sources & evidence

ORD record
ord-3474ad1e34df4508a8458a0a19302e6a
Source dataset
uspto-grants-1995_07
Patent number
US05430041

Reaction notes

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