Sodium Hydroxide → HCID 67915583, compound

HRID 847324Notes

Reaction equation

HRID 847324 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH2:13][C@@H:14]([CH:23]([CH3:25])[CH3:24])[CH2:15]/[CH:16]=[CH:17]/[C:18]([O:20]CC)=[O:19])[O:11][C:10]([CH3:27])([CH3:26])[N:9]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].S([O-])(O)(=O)=O.[K+].S([O-])([O-])(=O)=O.[K+].[K+]>O1CCOCC1>[C:31]([O:30][C:28]([N:9]1[C@@H:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C@H:12]([CH2:13][C@@H:14]([CH:23]([CH3:24])[CH3:25])[CH2:15]/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[O:11][C:10]1([CH3:26])[CH3:27])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24507Potassium SulfateHCID 516920Potassium bisulfateHCID 86746089HCID 86746089, compound

Product 1

HCID 67915583HCID 67915583, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.7 g (3.5 mmol) of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S,E)-5-(ethoxycarbonyl)-2-isopropyl-4-pentenyl]-2,2-dimethy--3-oxazolidinecarboxylate are dissolved in 20 ml of dioxan and treated with 7 ml (7.0 mmol) of 1N sodium hydroxide solution. Thereafter, the reaction mixture is stirred at 90° for 2.5 hours, cooled and poured into ice-water. Then, the reaction mixture is adjusted to pH 3 with a pH 2 buffer of potassium hydrogen sulphate and potassium sulphate and extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on 18 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 1.28 g of (E,S)-5-[[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]methyl]-6-methyl-2-heptenoic acid as an oil, MS: 436 (M-CH3)+.

Workup

  1. temperaturecooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride extracts are dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. additionChromatography of the residue on 18 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-9e29265705894e4883c11e9cc067b9bd
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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