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

HRID 1438788노트

반응식

HRID 1438788 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e4122d80b5b432bbd2a3e856f83ede9
출처 데이터셋
uspto-grants-1977_11
특허 번호
US04056521

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