Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-cyclohexyl-2(R)-(4-benzyloxy-benzyl)-hexanoic acid

HRID 1376662Notes

Reaction equation

HRID 1376662 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[CH2:18]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-:39]>COCCOC>[C:1]([NH:8][C@@H:9]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@@H:17]([OH:39])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:29]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 566153103(R)-[(4-Benzyloxyphenyl)methyl]-5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]dihydrofuran-2-one

Product 1

HCID 228742765(S)-(Boc-amino)-4(S)-hydroxy-6-cyclohexyl-2(R)-(4-benzyloxy-benzyl)-hexanoic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1 h), 2.4 g (4.728 mmol) of 5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]-3(R)-(4-benzyloxy-benzyl)-dihydrofuran-2-(3H)-one in 10 ml of 1,2-dimethoxyethane are reacted with 9.45 ml of 1M LiOH solution to give the title compound. The title compound is purified by crystallisation from hexane. TLC Rf (E)=0.33; tRet (III)=18 min; FAB-MS (M+H+)=526.

Workup

  1. customAnalogously to Example 1 h

Sources & evidence

ORD record
ord-337247d66ac64b2d9291e24ecc86d2eb
Source dataset
uspto-grants-1997_09
Patent number
US05663168

Reaction notes

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