Methanol → HCID 70593753, compound

HRID 1395486Notes

Reaction equation

HRID 1395486 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-1f57d838898c45d4b76d12abf781c2b1
Source dataset
uspto-grants-1980_05
Patent number
US04203897

Reaction notes

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