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

HRID 1377162Notes

Reaction equation

HRID 1377162 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][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[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-:38].[Li+]>C(COC)OC.O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:38])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:29]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 156595565(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one

Product 1

HCID 228742955(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(p-benzyloxyphenyl)methyl]-hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In analogy with Example 1i), 1.4 g (2.79 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one in 45 ml of dimethoxyethane and 23 ml of water are hydrolysed with 11 ml of a 1M lithium hydroxide solution. The reaction mixture, which has been partially evaporated, is poured onto a mixture of ice, 137 ml of sat. NH4Cl solution, 11 ml of 10% citric acid solution and 56 ml of methylene chloride, and methanol is added until the precipitated solid dissolves. The aqueous phase is extracted with 2 portions of methylene chloride/methanol, approximately 10:1, and the organic phases are washed with saline, dried with Na2SO4 and evaporated: tRet (I)=24.0 min; FAB-MS (M+H)+ =520.

Workup

  1. customThe reaction mixture, which has been partially evaporated
  2. additionis poured onto a mixture of ice, 137 ml of sat. NH4Cl solution, 11 ml of 10% citric acid solution and 56 ml of methylene chloride, and methanol
  3. additionis added until the precipitated solid
  4. dissolutiondissolves
  5. extractionThe aqueous phase is extracted with 2 portions of methylene chloride/methanol, approximately 10:1
  6. washthe organic phases are washed with saline
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customtRet (I)=24.0 min

Sources & evidence

ORD record
ord-672866a88f904d85b156395fd92c6b45
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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