Lithium Hydroxide → 5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,3,4-trimethoxyphenyl)-methyl]hexanoic acid

HRID 2394135Notes

Reaction equation

HRID 2394135 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][CH3:31])=[C:26]([O:32][CH3:33])[C:25]=2[O:34][CH3:35])[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-:36].[Li+]>C(COC)OC.O.[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)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:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[C:25]=1[O:34][CH3:35])[C:20]([OH:36])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 152958925(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one

Product 1

HCID 228742855(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,3,4-trimethoxyphenyl)-methyl]hexanoic acid

Reagents, catalysts & solvents 4

HCID 311Citric AcidSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 1.354 g (2.685 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 43.36 ml of dimethoxyethane and 21.86 ml of water is treated, at RT, with 10.74 ml of a 1M solution of lithium hydroxide in water, and this reaction mixture is stirred for 2 h. It is then transferred to a separating funnel, diluted with 132 ml of sat. ammonium chloride solution and 11 ml of a 10% citric acid solution (both cold), and this mixture is then extracted with ethyl acetate and a little THF. The title compound, which is dried under HV and subjected to further processing without being purified, is obtained after washing the organic phase with (cold) saline and drying it over sodium sulfate. TLC Rf (C)=0.03. MS (M-H2O)+ =485.

Workup

  1. customIt is then transferred to a separating funnel
  2. extractionis then extracted with ethyl acetate
  3. dry with materialThe title compound, which is dried under HV
  4. customwithout being purified
  5. customis obtained
  6. washafter washing the organic phase with (cold) saline
  7. dry with materialdrying it over sodium sulfate

Sources & evidence

ORD record
ord-c94b377a3d1e4705bc6b5b074c82a401
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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