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Trifluoroacetic acid → Benzylamine

HRID 372869
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HRID 372869 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].[C:41]1(OC)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.F[C:50](F)(F)[C:51](O)=O.C(O[CH2:60][CH3:61])(=O)C>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].[N:9]1[C:10]([CH3:39])=[CH:11][C:60]([CH3:61])=[CH:41][C:51]=1[CH3:50].[CH2:7]([NH2:9])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

생성물 3

HCID 7504BenzylamineHCID 79532,4,6-Trimethylpyridine
HCID 70617649
7-(2-Thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate (stereoisomer A: 58 mg) in methylene chloride (0.6 ml) are added anisole (0.12 ml) and trifluoroacetic acid (0.12 ml). After 15 minutes, the reaction mixture is concentrated at room temperature, and obtained residue is dissolved in ethyl acetate, and is extracted with aqueous sodium hydrogen carbonate solution. The extract aqueous solution is cooled with ice, stirred and neutralized with 1N-hydrochloric acid to pH 2, and is extracted with ethyl acetate. The extract solution is washed with water, dried over sodium sulfate, and concentrated to one third volume. To this solution is added an equivalent amount of collidine or benzylamine, and the separated crystals are collected by filtration to give 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid (stereoisomer A) collidine salt or benzylamine salt.

후처리

  1. concentrationthe reaction mixture is concentrated at room temperature
  2. customobtained residue
  3. extractionis extracted with aqueous sodium hydrogen carbonate solution
  4. temperatureThe extract aqueous solution is cooled with ice
  5. extractionis extracted with ethyl acetate
  6. washThe extract solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to one third volume
  9. additionTo this solution is added an equivalent amount of collidine or benzylamine
  10. filtrationthe separated crystals are collected by filtration

출처 및 근거

ORD 기록
ord-a9bba55a220144469d034be47b5d4100
출처 데이터셋
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04092474

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