Benzyl glyoxylate → 7-(Benzyloxycarbonyl-1-hydroxymethyl)-3-phenoxymethyl-6-oxo-2-thia-4,7-diazabicyclo[3,2,0]hept-3-ene

HRID 1759228Notes

Reaction equation

HRID 1759228 reaction equation
[O:1]([CH2:8][C:9]1[S:10][CH:11]2[CH:14]([N:15]=1)[C:13](=[O:16])[NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:20])[CH:18]=[O:19]>C1C=CC=CC=1>[CH2:22]([O:21][C:17]([CH:18]([N:12]1[CH:11]2[CH:14]([N:15]=[C:9]([CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:10]2)[C:13]1=[O:16])[OH:19])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11008258Benzyl glyoxylateHCID 125190673-(Phenoxymethyl)-4-thia-2,6-diazabicyclo[3.2.0]hept-2-EN-7-one

Product 1

HCID 142308107-(Benzyloxycarbonyl-1-hydroxymethyl)-3-phenoxymethyl-6-oxo-2-thia-4,7-diazabicyclo[3,2,0]hept-3-eneYield 514.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a 500 ml. flask equipped with a Dean-Stark condenser filled with Molecular Sieves 3A (™, manufactured by Nakarai Chemicals Ltd.) were charged with 3-phenoxymethyl-6-oxo-2-thia-4,7-diazabicyclo[3,2,0]hept-3-ene (995 mg.), benzyl glyoxylate (6.2 g.) and benzene (80 ml.). The mixture was heated under reflux for 3.5 hours. After benzene (40 ml.) was distilled off, the resultant solution was cooled to room temperature, and 25% aqueous solution of sodium bisulfite (150 ml.) was added thereto. The mixture was stirred for half an hour, and the precipitate was filtered off and washed with benzene. The organic layer was separated and washed twice with water (50 ml.) and twice with an aqueous solution of sodium chloride (150 ml.). Drying over magnesium sulfate and removal of the solvent gave an oil (8.7 g.) of 7-(1-benzyloxycarbonyl-1-hydroxymethyl)-3-phenoxymethyl-6-oxo-2-thia-4,7-diazabicyclo[3,2,0]hept-3-ene.

Workup

  1. customflask equipped with a Dean-Stark condenser
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3.5 hours
  4. distillationAfter benzene (40 ml.) was distilled off
  5. addition25% aqueous solution of sodium bisulfite (150 ml.) was added
  6. filtrationthe precipitate was filtered off
  7. washwashed with benzene
  8. customThe organic layer was separated
  9. washwashed twice with water (50 ml.) and twice with an aqueous solution of sodium chloride (150 ml.)
  10. dry with materialDrying over magnesium sulfate and removal of the solvent

Sources & evidence

ORD record
ord-85a67bac2a554748b8df628f9486900f
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

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