Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-(p-benzyloxyphenyl)-2(R)-(phenylmethyl)-hexanoic acid

HRID 263777Notes

Reaction equation

HRID 263777 reaction equation
[C:1]([NH:8][C@H:9]([C@H:25]1[O:29][C:28](=[O:30])[C@H:27]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:38].[Li+]>C(COC)OC.O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[C@@H:25]([OH:29])[CH2:26][C@@H:27]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:28]([OH:38])=[O:30])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15659558HCID 15659558, compound

Product 1

HCID 228742805(S)-(Boc-amino)-4(S)-hydroxy-6-(p-benzyloxyphenyl)-2(R)-(phenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1i), 0.502 g (1.00 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-(phenylmethyl)-dihydrofuran-2-(3H)-one in 16 ml of dimethoxyethane and 8.6 ml of water are hydrolysed with 4 ml of 1M lithium hydroxide solution. The reaction mixture, partially concentrated by evaporation, is poured onto a mixture of ice, 49 ml of sat. NH4Cl solution, 4.1 ml of 10% citric acid solution and methylene chloride, and ethanol is added until the precipitated solid has dissolved. The aqueous phase is extracted with 2 portions of methylene chloride/ethanol approximately 9:1, and the organic phases are washed with brine, dried with Na2SO4 and concentrated by evaporation: TLC Rf (A)=0.22.

Workup

  1. concentrationThe reaction mixture, partially concentrated by evaporation
  2. additionis poured onto a mixture of ice, 49 ml of sat. NH4Cl solution, 4.1 ml of 10% citric acid solution and methylene chloride, and ethanol
  3. additionis added until the precipitated solid
  4. dissolutionhas dissolved
  5. extractionThe aqueous phase is extracted with 2 portions of methylene chloride/ethanol approximately 9:1
  6. washthe organic phases are washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c45b9326005e4c16983b28e1ac19a7d0
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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