N-methyl-N-(trimethylsilyl)trifluoroacetamide → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1085088

반응식

HRID 1085088 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][CH3:30])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18]OC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.CN([Si](C)(C)C)C(=O)C(F)(F)F.[I:43][Si](C)(C)C>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][CH3:30])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][I:43])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

참가 물질

5

반응물 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 85247Trimethylsilyl iodideHCID 5742673Cefotaxime

생성물 1

HCID 14252931(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7β-[(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (977 mg) was suspended in methylene chloride (16 ml), followed by an addition of N-methyl-N-(trimethylsilyl) trifluoroacetamide (1350 μl). The resulting mixture was stirred at room temperature for 1 hour. After ice-cooling, iodotrimethylsilane (810 μl) was added and the resulting mixture was stirred for 15 minutes. The reaction mixture was concentrated under reduced pressure to obtain the silylated derivative of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylic acid.

후처리

  1. temperatureAfter ice-cooling
  2. stirringthe resulting mixture was stirred for 15 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e8783b6d6eb54542a12dccd68b8cb1ca
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008260

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