Sodium Bicarbonate → Cefazolin deacylated

HRID 1389685

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HRID 1389685 반응식
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9]OC(=O)CC(=O)C)[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].[SH:27][C:28]1[S:29][C:30]([CH3:33])=[N:31][N:32]=1>O>[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:27][C:28]3[S:29][C:30]([CH3:33])=[N:31][N:32]=3)[CH2:7][S:8][C@H:3]12

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 178434161HCID 178434161, 화합물

생성물 1

HCID 6350581Cefazolin deacylated수율 84.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

In water (30 ml) was dissolved 7β-amino-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (3.14 g) together-with sodium hydrogen carbonate (1.84 g) and 2-mercapto-5-methyl-1,3,4-thiadiazole (1.6 g) and the resultant solution was adjusted its pH to 6.4, followed by stirring for one hour at 60° C. After cooling, the reaction solution was washed with dichloromethane and pH of the aqueous layer was adjusted to 3.5 under ice-cooling, followed by stirring for one hour. The precipitated materials were collected by filtration and washed with water, methanol and acetone in this order, followed by drying to give 7β-amino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.9 g).

후처리

  1. temperatureAfter cooling
  2. washthe reaction solution was washed with dichloromethane and pH of the aqueous layer
  3. temperaturecooling
  4. stirringby stirring for one hour
  5. filtrationThe precipitated materials were collected by filtration
  6. washwashed with water, methanol and acetone in this order
  7. customby drying

출처 및 근거

ORD 기록
ord-1c6bff5f421e423c8348e19cbc49b1be
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04245088

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