Dichloromethane → (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755865노트

반응식

HRID 1755865 반응식
[OH:1][NH:2][C:3]([C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([SH:13])[N:7]2[N:6]=1)=[O:4].CC(O[CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O.B(F)(F)F.CCOCC.ClCCl>S1(CCCC1)(=O)=O.ClCCl>[NH2:28][C@@H:25]1[C:26](=[O:27])[N:23]2[C@@H:24]1[S:29][CH2:30][C:21]([CH2:20][S:13][C:12]1[N:7]3[N:6]=[C:5]([C:3](=[O:4])[NH:2][OH:1])[N:15]=[C:8]3[N:9]=[C:10]([CH3:14])[CH:11]=1)=[C:22]2[C:31]([OH:33])=[O:32]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178429721HCID 178429721, 화합물

생성물 1

HCID 22855051(6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

시약·촉매·용매 1

HCID 69712587Dichloromethane sulpholane용매

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온도
0 °C

실험 절차

N-Hydroxy-7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide and 3.4 g (12.5 mmol) of 7-aminocephalosporanic acid (3.1 g) (13.9 mmol) are suspended in 75 ml of sulpholane/dichloromethane (1:1 v/v). 7.5 ml of boron trifluoride etherate are added dropwise thereto at 0° C. and the mixture is stirred at 0° C. for 2.5 hours and at room temperature for 15 hours. 200 ml of dichloromethane are now added. After stirring for 30 minutes the mixture is suction filtered. The filter material is dissolved in 100 ml of water. The product is precipitated with saturated sodium hydrogen carbonate solution (pH~5), filtered off and washed with water, ethanol and ether. There are obtained 3.5 g of (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

후처리

  1. stirringAfter stirring for 30 minutes the mixture
  2. filtrationfiltered
  3. dissolutionThe filter material is dissolved in 100 ml of water
  4. customThe product is precipitated with saturated sodium hydrogen carbonate solution (pH~5)
  5. filtrationfiltered off
  6. washwashed with water, ethanol and ether

출처 및 근거

ORD 기록
ord-b3576f4a2abd4f508fb1e720816d09dc
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438052

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