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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Dichloromethane → (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-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 1755904
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인쇄 미리보기

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HRID 1755904 반응식
[SH:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([NH:13][OH:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH2:15][OH:16])[CH:3]=1.CC(O[CH2:21][C:22]1[CH2:31][S:30][C@@H:25]2[C@H:26]([NH2:29])[C:27](=[O:28])[N:24]2[C:23]=1[C:32]([OH:34])=[O:33])=O.B(F)(F)F.CCOCC.ClCCl>S1(CCCC1)(=O)=O.ClCCl>[NH2:29][C@@H:26]1[C:27](=[O:28])[N:24]2[C@@H:25]1[S:30][CH2:31][C:22]([CH2:21][S:1][C:2]1[N:7]3[N:8]=[C:9]([C:11](=[O:12])[NH:13][OH:14])[N:10]=[C:6]3[N:5]=[C:4]([CH2:15][OH:16])[CH:3]=1)=[C:23]2[C:32]([OH:34])=[O:33]
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참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178523964HCID 178523964, 화합물

생성물 1

HCID 22855050(6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid수율 66.9%

시약·촉매·용매

1
HCID 69712587Dichloromethane sulpholane용매

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온도
0 °C

실험 절차

7-Mercapto-N-hydroxy-5-(hydroxymethyl)-s-triazolo[1,5-a]pyrimidine-2-carboxamide (300 mg) (1.24 mmol) and 305 mg (1.12 mmol) of 7-aminocephalosporanic acid are suspended in 50 ml of sulpholane/dichloromethane (1:1 v/v). 5 ml of boron trifluoride diethyl etherate are added thereto at 0° C. The reaction mixture is stirred at 0° C. for 21/2 hours and at room temperature for 24 hours. After the addition of 30 ml of dichloromethane the mixture is stirred for 15 minutes and subsequently filtered. The suction filter material is dissolved in water and adjusted to pH 5 with saturated aqueous sodium hydrogen carbonate solution. The precipitated product is filtered off under suction and washed in succession with water, dichloromethane and diethyl ether. There are obtained 340 mg of (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-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. customat 0° C
  2. waitat room temperature for 24 hours
  3. stirringis stirred for 15 minutes
  4. filtrationsubsequently filtered
  5. filtrationThe suction filter material
  6. dissolutionis dissolved in water
  7. filtrationThe precipitated product is filtered off under suction
  8. washwashed in succession with water, dichloromethane and diethyl ether

출처 및 근거

ORD 기록
ord-2584516e3fd94a03b22b961a7bc29f10
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05438052

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