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

HRID 1377143Notes

Reaction equation

HRID 1377143 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][CH3:39])=[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-:40].[Li+].[CH2:42]([CH2:45][O:46][CH3:47])OC>O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:47]([O:46][CH2:45][C:42]2[CH:26]=[CH:25][CH:9]=[CH:10][CH:11]=2)=[CH:13][CH:12]=1)[C@@H:25]([OH:40])[CH2:26][C@@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[C:28]([OH:29])=[O:30])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 701494225(S)-[1(S)-(Boc-Amino)-2-(p-benzyloxyphenyl)ethyl]-3(R)-[(p-methoxyphenyl)-methyl]dihydrofuran-2-(3H)-one

Product 1

HCID 228764025(S)-(Boc-Amino)-4(S)-hydroxy-6-(p-benzyloxyphenyl)-2(R)-[(p-methoxyphenyl)-methyl]hexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g (4.89 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxy-phenyl)-ethyl]-3(R)-[(p-methoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 50 ml of dimethoxyethane are hydrolysed, under an N2 atmosphere, with 19.6 ml of a 1M lithium hydroxide solution in water. After 25 h at RT, the dimethoxyethane is evaporated off on a RE, and the residue is treated with an ice-cold mixture of 150 ml of sat. NH4Cl solution, 25 ml of 10% citric acid solution and methylene chloride. The aqueous phase is separated off and extracted 2× with methylene chloride. The organic phases are washed with saline, dried with Na2SO4 and evaporated to give the title compound: TLC Rf (B)=0.28; tRet (II)=16.4 min.

Workup

  1. customthe dimethoxyethane is evaporated off on a RE, and the residue
  2. additionis treated with an ice-cold mixture of 150 ml of sat. NH4Cl solution, 25 ml of 10% citric acid solution and methylene chloride
  3. customThe aqueous phase is separated off
  4. extractionextracted 2× with methylene chloride
  5. washThe organic phases are washed with saline
  6. dry with materialdried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-cf3404eb880f4f54b1b36238f70dd7aa
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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