Acetic Acid → HCID 57134054, compound

HRID 1075225Notes

Reaction equation

HRID 1075225 reaction equation
C([O:9][C@@H:10]([C@@H:12]1[C@@H:15]([S:16][CH3:17])[N:14]([C:18]([C:22]([O:24][CH3:25])=[O:23])=[C:19]([CH3:21])[CH3:20])[C:13]1=[O:26])[CH3:11])(=O)C1C=CC=CC=1.[Na].C(O)(=O)C>CO.C(OCC)(=O)C>[OH:9][C@@H:10]([C@@H:12]1[C@@H:15]([S:16][CH3:17])[N:14]([C:18]([C:22]([O:24][CH3:25])=[O:23])=[C:19]([CH3:20])[CH3:21])[C:13]1=[O:26])[CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 57068111HCID 57068111, compound

Product 1

HCID 57134054HCID 57134054, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

91 mg (0.24 mmole) of (3S, 4R)-3-[(R)-1-benzoyloxyethyl]-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2-one were dissolved in 1 ml of methanol. To the resulting solution was added a solution of 7.17 mg (0.31 mmole) of sodium in 0.65 ml of methanol at 0° C., and then the mixture was stirred at room temperature (18°-20° C.) for 5 hours. After completion of the reaction, the mixture was made slightly acidic by the addition of acetic acid, diluted with 20 ml of ethyl acetate and washed with water. After drying the mixture, the solvent was distilled off. The resulting residue was subjected to preparative thin layer chromatography on silica gel developed with a 2:1 by volume mixture of benzene and ethyl acetate to give 50 mg (yield 74.4%) of the pure product as an oil, which was proved by nuclear magnetic resonance spectroscopy to be an approximately 4:1 mixture of the 1'R- and 1'S-isomers.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water
  3. customAfter drying the mixture
  4. distillationthe solvent was distilled off
  5. additiondeveloped with a 2:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-f0528e80665b456eb025897daeee43a6
Source dataset
uspto-grants-1983_07
Patent number
US04395418

Reaction notes

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