Lithium Hydroxide → 5(S)-Tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid

HRID 725632Notes

Reaction equation

HRID 725632 reaction equation
[OH-:1].[Li+].[C:3]([O:7][C:8]([NH:10][C@H:11]([CH:32]1[CH2:36][C@@H:35]([CH3:37])[C:34](=[O:38])[O:33]1)[CH2:12][C@@H:13]([CH:29]([CH3:31])[CH3:30])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>COCCOC.O>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:12][C@@H:13]([CH:29]([CH3:31])[CH3:30])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)[C@@H:32]([OH:1])[CH2:36][C@@H:35]([CH3:37])[C:34]([OH:33])=[O:38])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 228657322-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

Product 1

HCID 228658195(S)-Tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

28.5 ml of 1N lithium hydroxide solution are added to 3.6 g of 2-{1(S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one in 210 ml of 1,2-dimethoxyethane/water (2:1) at room temperature. The reaction mixture is stirred at room temperature for a further 1 hour and then concentrated by evaporation. Ice and 10% aqueous citric acid solution are added to the residue. Repeated extraction with chloroform yields the crude title compound: Rf (ethyl acetate/hexane=1:1)=0.05; HPLC Rt =16.41 minutes.

Workup

  1. concentrationconcentrated by evaporation
  2. additionIce and 10% aqueous citric acid solution are added to the residue
  3. extractionextraction with chloroform

Sources & evidence

ORD record
ord-6280f2e3a5ab4da2b35c15b1624b3910
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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