Acetic Acid → HCID 54216548, compound

HRID 847314Notes

Reaction equation

HRID 847314 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][C@@H:21]([CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:23][C:24]([O:26]CC)=[O:25])[O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>CO>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C@H:11]([CH2:20][C@@H:21]([CH:29]([CH3:30])[CH3:31])[CH:22]=[CH:23][C:24]([OH:26])=[O:25])[O:10][C:9]1([CH3:32])[CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 53747735HCID 53747735, compound

Product 1

HCID 54216548HCID 54216548, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.7 g (3.7 mmol) of ethyl (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoate are dissolved in 10 ml of methanol, treated with 2 ml (18 mmol) of 28% sodium hydroxide solution and stirred at room temperature for 16 hours. Thereafter, the reaction mixture is poured into ice-water, the pH value is adjusted to 5 with acetic acid and the mixture is extracted with ethyl acetate. The ethyl acetate extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on 20 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 1.2 g of (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoic acid as an oil, MS: 422 (M-CH3)+.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe ethyl acetate extracts are dried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. additionChromatography of the residue on 20 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-ddbfdf09b2ef4c19a2a15bd0527db500
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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