Lithium Hydroxide → 5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,4-difluorophenyl)methyl]hexanoic acid

HRID 263788Notes

Reaction equation

HRID 263788 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]([F:30])=[CH:26][C:25]=2[F:31])[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:32].[Li+]>C(COC)OC.O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:32])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 701499395(S)-[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(2,4-difluorophenyl)methyl]dihydrofuran-2-(3H)-one

Product 1

HCID 228742865(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,4-difluorophenyl)methyl]hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1i), 3.1 g (7.18 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,4-difluorophenyl)methyl]-dihydrofuran-2-(3H)-one in 77 ml of dimethoxyethane and 19 ml of water are hydrolysed with 28.7 ml of 1M lithium hydroxide solution (19 h RT): tRet (I)=14.7 min.

Sources & evidence

ORD record
ord-f0ed57edcf5f47e3b4661ed56f5cde4a
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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