HCID 53918863, compound → HCID 14257300, compound

HRID 2231537Notes

Reaction equation

HRID 2231537 reaction equation
C(O[C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C.[Na].[C:31]([O:35][CH3:36])(=[O:34])[CH2:32][SH:33]>CO>[CH3:36][O:35][C:31]([CH2:32][S:33][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:34]

Participants

4

Reactant 2

HCID 53918863HCID 53918863, compoundHCID 86741499HCID 86741499, compound

Product 1

HCID 14257300HCID 14257300, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.93 g of (3S,4S)-4-acetoxy-3-tritylamino-2-oxoazetidine in 100 ml of methanol is added a solution of 0.64 g of methyl thioglycolate sodium salt with stirring under ice-cooling. After 1 hour, the solvent is distilled off and the residue is dissolved in ethyl acetate. The solution is washed with water, then the solvent is distilled off, and the residue is purified by silica gel column-chromatography (methylene chloride:ethyl acetate=11:1) to give 1.38 g of (3R4R)-4-methoxycarbonylmethylthio-3-tritylamino-2-oxoazetidine (A) and 0.92 g of the corresponding (3R,4S)-isomer (B)

Workup

  1. temperaturecooling
  2. distillationthe solvent is distilled off
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe solution is washed with water
  5. distillationthe solvent is distilled off
  6. customthe residue is purified by silica gel column-chromatography (methylene chloride:ethyl acetate=11:1)

Sources & evidence

ORD record
ord-345b1ee86a9544ae80010a7ec05aede0
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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