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Acetone → 2,2,2-Trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate

HRID 1438794
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HRID 1438794 반응식
Br[CH2:2][CH2:3][C:4]1(C)[CH:8]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:7]2[C:17](=[O:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:6]2[S:5]1.[N-:31]=[N+:32]=[N-:33].[Na+].CC(C)=O>O>[N:31]([C:3]1([CH3:2])[CH:8]([C:9]([O:11][CH2:12][C:13]([Cl:15])([Cl:14])[Cl:16])=[O:10])[N:7]2[C:17](=[O:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:6]2[S:5][CH2:4]1)=[N+:32]=[N-:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 705961582,2,2-Trichloroethyl 2-bromoethyl-2-methyl-6-(2-phenyl-acetamido)penam-3-carboxylate

생성물 1

HCID 867333872,2,2-Trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate수율 17.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2,2,2-trichloroethyl 2-bromoethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.08 g), sodium azide (0.26 g), acetone (20 ml) and water (4 ml) was stirred for 4 hours at room temperature. After acetone was distilled off under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water, with saturated sodium bicarbonate aqueous solution and further with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure and a small quantity of ether was added to the residue to give colorless crystals of 2,2,2,-trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (170 mg). This substance was recrystallized from carbon tetrachloride to give crystals melting at 136° to 140° C.

후처리

  1. distillationAfter acetone was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water, with saturated sodium bicarbonate aqueous solution and further with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. additiona small quantity of ether was added to the residue

출처 및 근거

ORD 기록
ord-b38d225e193446e0974e3114040d8dea
출처 데이터셋
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04056521

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