Citric Acid → 5(s)-(Boc-amino)-4(s)-hydroxy-6-(p-methoxyphenyl)-2(r)-(phenylmethyl)hexanoic acid

HRID 2394105Notes

Reaction equation

HRID 2394105 reaction equation
[C:1]([NH:8][C@H:9]([C@H:19]1[O:23][C:22](=[O:24])[C@H:21]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20]1)[CH2:10][C:11]1[CH:16]=CC(OC)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Li+].[NH4+].[Cl-].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:39].[CH2:49]([CH2:52][O:53][CH3:54])OC>O.CO.C(Cl)Cl>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:49][C:52]([O:53][CH3:54])=[CH:13][CH:12]=1)[C@@H:19]([OH:39])[CH2:20][C@@H:21]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:22]([OH:23])=[O:24])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 25517Ammonium ChlorideHCID 701496385(S)-[1(S)-(Boc-Amino)-2-(p-methoxyphenyl)ethyl]-3(R)-(phenylmethyl)dihydrofuran-2-(3H)-one

Product 1

HCID 228764105(s)-(Boc-amino)-4(s)-hydroxy-6-(p-methoxyphenyl)-2(r)-(phenylmethyl)hexanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.00 g (7.05 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-methoxy-phenyl)-ethyl]-3(R)-(phenylmethyl)dihydrofuran-2-(3H)-one in 112 ml of dimethoxyethane and 57 ml of water are hydrolysed, under protective gas, with 28 ml of 1M lithium hydroxide solution. After 20 h at RT, the reaction mixture is poured onto an ice-cold mixture of 340 ml of sat. NH4Cl solution, 28 ml of 10% citric acid solution and 140 ml of methylene chloride. Methanol is added in order to dissolve the product completely. The aqueous phase is separated off and extracted 2× with methylene chloride. The organic phases are washed with saline, dried with Na2SO4 and evaporated, with the title compound being obtained: tRet (II)=14.0 min; FAB-MS (M+H)+ =444.

Workup

  1. dissolutionto dissolve the product completely
  2. customThe aqueous phase is separated off
  3. extractionextracted 2× with methylene chloride
  4. washThe organic phases are washed with saline
  5. dry with materialdried with Na2SO4
  6. customevaporated, with the title compound
  7. custombeing obtained

Sources & evidence

ORD record
ord-20670b8fc9e44f95806d30224b93e38b
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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