Sodium cyanoborohydride → 1-[N-(1-Carboethoxy-3-p-chlorophenylpropyl)-(S)-alanyl]-hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

HRID 2226424Notes

Reaction equation

HRID 2226424 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][CH:8]2[CH2:14][O:15][CH2:16][CH:7]12)=[O:5])[CH3:3].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>C(O)C>[C:27]([CH:26]([NH:1][C@H:2]([C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][CH:8]2[CH2:14][O:15][CH2:16][CH:7]12)=[O:5])[CH3:3])[CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([Cl:17])=[CH:23][CH:22]=1)([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 13201328Ethyl 4-(4-chlorophenyl)-2-oxobutanoateHCID 186548901-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

Product 1

HCID 867481491-[N-(1-Carboethoxy-3-p-chlorophenylpropyl)-(S)-alanyl]-hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat 1-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2-(S)-carboxylic acid (prepared as described in Example 47) and ethyl 4-(p-chlorophenyl)-2-oxobutyrate with sodium cyanoborohydride as described in Example 47D (ethanol solvent) to obtain the title compound.

Sources & evidence

ORD record
ord-32e21e4980354475b00ca99b94b9f7fc
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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