Methanol → HCID 70593753, compound

HRID 261245Notes

Reaction equation

HRID 261245 reaction equation
[O:1]=[C:2]1[CH:5]([NH:6][C:7](=[O:16])[CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]([S:17]NC2C=CC=CC=2)[N:3]1[CH:25]([C:30]([CH3:32])=[CH2:31])[C:26]([O:28][CH3:29])=[O:27].CO.B(F)(F)F.C[CH2:40][O:41]CC>C(Cl)Cl>[CH3:40][O:41][CH2:31][C:30]1([CH3:32])[CH:25]([C:26]([O:28][CH3:29])=[O:27])[N:3]2[C:2](=[O:1])[CH:5]([NH:6][C:7](=[O:16])[CH2:8][O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@H:4]2[S:17]1

Participants

5

Reactant 3

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 23345945HCID 23345945, compound

Product 1

HCID 70593753HCID 70593753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-oxo-3-(2-phenoxyacetamido)-4-anilinothio-α-isopropenyl-1-azetidineacetate (454 mg) was dissolved in methylene chloride (20 ml). To this solution were added methanol (5 ml) and then boron trifluoride etherate (0.124 g) under cooling at 0° C. The mixture was stirred for 3 hours at the same temperature and further stirred for 2 hours at 5° to 10° C. After the reaction, the reaction mixture was washed with 5% sodium bicarbonate aqueous solution and then with water, dried and the solvent was distilled off. The oily residue (25 g) was subjected to column chromatography on silica gel and eluted with chloroform. The eluate was separated into each 50 ml fraction and the seventh and eighth fractions were combined. The solvent was distilled off to give oily methyl 2-methoxymethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate.

Workup

  1. stirringfurther stirred for 2 hours at 5° to 10° C
  2. customAfter the reaction
  3. washthe reaction mixture was washed with 5% sodium bicarbonate aqueous solution
  4. dry with materialwith water, dried
  5. distillationthe solvent was distilled off
  6. washeluted with chloroform
  7. customThe eluate was separated into each 50 ml fraction
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-06b184c9c612422fa027743d38594bbe
Source dataset
uspto-grants-1979_08
Patent number
US04164497

Reaction notes

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