Methanol → HCID 70593753, compound

HRID 1856161Notes

Reaction equation

HRID 1856161 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 g) 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 to 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 to 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-b2b0e9fd2eea4c2e8279162ac58a8c0b
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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