Ethyl Acetate → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

HRID 1660594노트

반응식

HRID 1660594 반응식
P(Cl)(Cl)Cl.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:8]2[S:7]1=O.C(OCC)(=O)C>CN(C)C=O>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][C:16]([Cl:17])([Cl:18])[Cl:19])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@H:8]2[S:7]1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 705266812,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide

생성물 1

HCID 705273932,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate수율 61.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Phosphorus trichloride (0.5 ml.) was dropwise added under ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide (0.72 g.) in dimethylformamide (5 ml.) and the mixture was stirred for 1 hour at the same temperature. After the reaction, the reaction mixture was poured into a mixture of ethyl acetate (40 ml.) and ice-water (40 ml.), and the ethyl acetate layer was separated. The aqueous layer was further extracted with ethyl acetate (10 ml.), and the ethyl acetate layer was combined. The combined solution was washed in turn with 5% hydrochloric acid, a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The dried solution was treated with activated charcoal and the solvent was distilled off. The residue was crystallized with a small amount of ether to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (0.43 g.), mp 175° to 178° C.

후처리

  1. customAfter the reaction
  2. customthe ethyl acetate layer was separated
  3. extractionThe aqueous layer was further extracted with ethyl acetate (10 ml.)
  4. washThe combined solution was washed in turn with 5% hydrochloric acid
  5. dry with materiala sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  6. additionThe dried solution was treated with activated charcoal
  7. distillationthe solvent was distilled off
  8. customThe residue was crystallized with a small amount of ether

출처 및 근거

ORD 기록
ord-4a5ff27174064c4d9af26aa507eac33d
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04308380

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