Potassium Carbonate → HCID 53785237, compound

HRID 597488Notes

Reaction equation

HRID 597488 reaction equation
Br[CH2:2][C:3](=[O:21])[CH2:4][S:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH:11][C:12](=[O:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:21]=[C:3]1[CH2:2][N:9]2[C:8](=[O:10])[C@@H:7]([NH:11][C:12](=[O:20])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:6]2[S:5][CH2:4]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22796652HCID 22796652, compound

Product 1

HCID 53785237HCID 53785237, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (3R,4R)-4-(3'-bromoacetonylthio)-3-phenylacetamidoazetidin-2-one (1 g., 2.7 mmole) in acetone (50 ml.) with potassium carbonate (2 g., 14.5 mmole) was stirred at 4° for 16 hours and at 22° for 4 hours. The mixture was filtered and evaporated under reduced pressure. The resulting gum was chromatographed on silica gel (10 × 4 cm.) with Analar chloroform as solvent to give a pale-yellow foam. Crystallisation from ethyl acetate gave (6R,7R)-3-keto-7-phenylacetamidocepham (0.1 g., 12.5%). M.p. I.R. and NMR in agreement with standard obtained from material prepared in Example 3.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe resulting gum was chromatographed on silica gel (10 × 4 cm.) with Analar chloroform as solvent
  4. customto give a pale-yellow foam
  5. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a7c8049674ae4e5a9caf4a912401beca
Source dataset
uspto-grants-1977_03
Patent number
US04014872

Reaction notes

Loading…