Boron trifluoride etherate → 7-Amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 34493

反応式

HRID 34493 の反応式
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[S:19]1[N:23]=[CH:22][C:21]([S-:24])=[N:20]1.[K+].B(F)(F)F.CCOCC>FC(F)(F)C(O)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:24][C:21]3[CH:22]=[N:23][S:19][N:20]=3)[CH2:15][S:14][C@H:9]12

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 23683003Potassium 1,2,5-thiadiazole-3-thiolate

生成物 1

HCID 678873867-Amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acid収率 73%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

7-Aminocephalosporanic acid (0.272 g) was added to the solution of potassium 1,2,5-thiadiazole-3-thiolate (0.136 g) in trifluoroacetic acid (5 ml) and the mixture was stirred for a few minutes until the solution turned clear, and then, boron trifluoride etherate (0.434 g) was added thereto and the mixture was stirred for 12 hours at room temperature. The reaction mixture was evaporated under reduced pressure and the residue was adjusted to pH 3.0 with 2% aqueous solution of ammonium hydroxide. The precipitates were collected by filtration, washed with cool water, acetone and diethyl ether and dried to give 7-amino-3-(1,2,5-thiadiazol-3-yl)thiomethyl-3-cephem-4-carboxylic acid (0.210 g).

後処理

  1. stirringthe mixture was stirred for 12 hours at room temperature
  2. customThe reaction mixture was evaporated under reduced pressure
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with cool water, acetone and diethyl ether
  5. customdried

出典と根拠

ORDレコード
ord-6c2d6420f00c4542bcf483518e402c71
出典データセット
uspto-grants-1988_08
特許番号
US04761410

関連ノート

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