Ethanol → 4-(N-benzyloxycarbonyl-L-valyloxy)benzoic acid

HRID 989941Notes

Reaction equation

HRID 989941 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([O:25]CC2C=CC(OC)=CC=2)=[O:24])=[CH:21][CH:20]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:35][CH:36]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 233875464-Methoxybenzyl 4(N-benzyloxycarbonyl-L-valyloxy)benzoate

Product 1

HCID 544688514-(N-benzyloxycarbonyl-L-valyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzyl 4-(N-benzyloxycarbonyl-L-valyloxy)benzoate was de-esterified by the method described in Example A-I-1, step c. The title compound (1.86 g) was obtained after silica gel column chromatography (2, 10, 20% ethanol in dichloromethane). Rf (2%MeOH/CHCl3) 0.20. The compound can be activated and esterifed directly to a drug or further modified as described below.

Sources & evidence

ORD record
ord-269ce38a4f57460aacf666cb7bee0faa
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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