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Ammonia → 7-amino-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 2412578
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HRID 2412578 반응식
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.[C:19]([C:22](=[N:30][OH:31])[CH2:23][N:24]1[C:28]([SH:29])=[N:27][N:26]=[N:25]1)([OH:21])=[O:20].B(F)(F)F.CCOCC.N>C(#N)C.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:29][C:28]3[N:24]([CH2:23][C:22]([C:19]([OH:21])=[O:20])=[N:30][OH:31])[N:25]=[N:26][N:27]=3)[CH2:15][S:14][C@H:9]12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178525592HCID 178525592, 화합물

생성물 1

HCID 1317132427-amino-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid수율 75.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6342Acetonitrile용매

실험 절차

To a suspension of 7-aminocephalosporanic acid (12.1 g) and 1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazole-5-thiol (9.0 g) in dry acetonitril (60 ml) was added boron trifluoride etherate (25.1 g) and the resulting solution was stirred at 50° for 50 minutes. Water (60 ml) was added and the solution was adjusted to pH 3.5 with conc. aqueous ammonia to give precipitates which were filtered, washed successively with water and acetone, and air-dried to give 7-amino-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (13.92 g).

후처리

  1. customto give
  2. customprecipitates which
  3. filtrationwere filtered
  4. washwashed successively with water and acetone
  5. customair-dried

출처 및 근거

ORD 기록
ord-c461c84710714baebc03f0e9fe8eb16b
출처 데이터셋
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04493834

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