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

HRID 1377124Notes

Reaction equation

HRID 1377124 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

2.7 g (4.43 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)ethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one in 59 ml of dimethoxyethane and 31.8 ml of water are treated, while excluding air, with 14.8 ml of a 1M lithium hydroxide solution. The mixture is then stirred at RT for 3 h and partially evaporated. The residue 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 dissolves. The aqueous phase is separated off and extracted with 2 portions of ethyl acetate, and the organic phases are washed with saline, dried with Na2SO4, evaporated and digested in hexane: TLC Rf (C)=0.07.

Workup

  1. custompartially evaporated
  2. additionThe residue 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
  3. additionis added until the precipitated solid
  4. dissolutiondissolves
  5. customThe aqueous phase is separated off
  6. extractionextracted with 2 portions of ethyl acetate
  7. washthe organic phases are washed with saline
  8. dry with materialdried with Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-a6445dbd6a9d40db88082241614d25c6
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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