Citric Acid → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(o-fluorophenylmethyl)-hexanoic acid

HRID 263783Notes

Reaction equation

HRID 263783 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]=[CH:26][C:25]=2[F:30])[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-].[Li+].[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:38]>C(COC)OC>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])[C:20]([OH:38])=[O:22])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 701493485(S)[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(o-fluorophenyl)methyl]dihydrofuran-2-(3H)-one

Product 1

HCID 228742945(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(o-fluorophenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1i), 4.5 g (10.8 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(o-fluorophenylmethyl)-dihydrofuran-2-(3H)-one in 170 ml of dimethoxyethane are hydrolysed with 43.5 ml of 1M lithium hydroxide solution. The evaporation residue of the reaction mixture is poured onto a mixture of ice, 120 ml of sat. ammonium chloride solution and 240 ml of 10% citric acid solution, and extracted with 3 portions of methylene chloride. The organic phases are washed with water and brine, dried over Na2SO4 and concentrated by evaporation: tRet (I)=14.5 min.

Workup

  1. extractionextracted with 3 portions of methylene chloride
  2. washThe organic phases are washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by evaporation
  5. customtRet (I)=14.5 min.

Sources & evidence

ORD record
ord-660d3335def54eb9a58bfae2831b344b
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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