m-Chloroperbenzoic acid → 2,2,2-Trichloroethyl 2chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxide

HRID 1438788Notes

Reaction equation

HRID 1438788 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]([Cl:40])([Cl:39])[CH2:14][O:15][C:16]([CH:18]1[N:22]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:21]2[S:20][C:19]1([CH2:37][Cl:38])[CH3:36])=[O:17]>C(Cl)(Cl)Cl>[Cl:38][CH2:37][C:19]1([CH3:36])[CH:18]([C:16]([O:15][CH2:14][C:13]([Cl:39])([Cl:12])[Cl:40])=[O:17])[N:22]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:21]2[S:20]1=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705905452,2,2-Trichloroethyl 2chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (2.03 g) in chloroform (30 ml) was added dropwise to a solution of 2,2,2-trichloroethyl-2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (5.0 g) in chloroform (40 ml) at -10°--5° C under stirring and then the mixture was stirred at -10°--5° C for 1 hour. After the solid was filtered off, the filtrate was washed with a saturated sodium becarbonate aqueous solution and water, in turn, and then dried over magnesium sulfate. After removal of solvent, the residue was crystallized by adding ethanol. The crystal was filtered and recrystallized from ethanol to give 2,2,2-trichloroethyl 2chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxide (4.10 g), mp 130°--131° C.

Workup

  1. stirringthe mixture was stirred at -10°--5° C for 1 hour
  2. filtrationAfter the solid was filtered off
  3. washthe filtrate was washed with a saturated sodium becarbonate aqueous solution and water, in turn
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was crystallized
  7. additionby adding ethanol
  8. filtrationThe crystal was filtered
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9e4122d80b5b432bbd2a3e856f83ede9
Source dataset
uspto-grants-1977_11
Patent number
US04056521

Reaction notes

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