Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid

HRID 263785Notes

Reaction equation

HRID 263785 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][CH:27]=[C:26]([F:30])[CH:25]=2)[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-:31].[Li+]>C(COC)OC>[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:31])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 677187205(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-fluorophenylmethyl)-dihydrofuran-2-(3H)-one

Product 1

HCID 228742925(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-fluorophenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1i), 3.7 g (8.95 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-fluorophenylmethyl)-dihydrofuran-2-(3H)-one in 140 ml of dimethoxyethane are hydrolysed with 35.8 ml of 1M lithium hydroxide solution. Extraction of the evaporation residue of the reaction mixture from a mixture of ice, 120 ml of sat. ammonium chloride solution and 240 ml of 10% citric acid solution with a large amount of methylene chloride (solubility!) yields the title compound: tRet (I)=14.6 min.

Workup

  1. extractionExtraction of the evaporation residue of the reaction mixture
  2. additionfrom a mixture of ice, 120 ml of sat. ammonium chloride solution and 240 ml of 10% citric acid solution with a large amount of methylene chloride (solubility!)

Sources & evidence

ORD record
ord-3489042a7d30400f9a301f3879abe382
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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