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

HRID 263780Notes

Reaction equation

HRID 263780 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][C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:34][CH:33]=2)[CH2:26]1)[CH2:10][C:11]1[CH:16]=[CH:15]C(OCC2C=CC=CC=2)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:46].[Li+].[CH2:48]([CH2:51][O:52][CH3:53])OC>O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:53]([O:52][CH2:51][C:48]2[CH:26]=[CH:25][CH:9]=[CH:10][CH:11]=2)=[CH:13][CH:12]=1)[C@@H:25]([OH:46])[CH2:26][C@@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:34][CH:33]=1)[C:28]([OH:29])=[O:30])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 156595605(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-(p-benzyloxyphenylmethyl)-dihydrofuran-2-(3H)-one

Product 1

HCID 228742795(S)-(Boc-Amino)-4(S)-hydroxy-6-(p-benzyloxyphenyl)-2(R)-[(p-benzyloxyphenyl)methyl]hexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Analogously to Example 1i), 2.7 g (4.43 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-(p-benzyloxyphenylmethyl)dihydrofuran-2-(3H)-one in 59 ml of dimethoxyethane and 31.8 ml of water are hydrolysed with 14.8 ml of 1M lithium hydroxide solution. The reaction mixture, partially concentrated by evaporation, is poured onto a mixture of ice, 181 ml of sat. NH4Cl solution, 16.2 ml of 10% citric acid solution and 400 ml of ethyl acetate, and THF is added until the precipitated solid has dissolved. The aqueous phase is extracted with 2 portions of ethyl acetate, and the organic phases are washed with brine, dried with Na2SO4, concentrated by evaporation and digested in hexane: TLC Rf (A)=0.07.

Workup

  1. concentrationThe reaction mixture, partially concentrated by evaporation
  2. additionis poured onto a mixture of ice, 181 ml of sat. NH4Cl solution, 16.2 ml of 10% citric acid solution and 400 ml of ethyl acetate, and THF
  3. additionis added until the precipitated solid
  4. dissolutionhas dissolved
  5. extractionThe aqueous phase is extracted with 2 portions of ethyl acetate
  6. washthe organic phases are washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c7f517b84e9645ca97070b444daa484d
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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