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Pyridine → benzhydryl (6R,7R)-3-(bromomethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 2231989
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HRID 2231989 반응식
Cl.[NH2:2][C@@H:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Br:11])[CH2:8][S:9][C@H:4]12.[C:30]([NH:49][C:50]1[S:51][CH:52]=[C:53](/[C:55](=[N:59]/[O:60][CH3:61])/[C:56](O)=[O:57])[N:54]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:11][CH2:10][C:7]1[CH2:8][S:9][C@@H:4]2[C@H:3]([NH:2][C:56](=[O:57])/[C:55](/[C:53]3[N:54]=[C:50]([NH:49][C:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[S:51][CH:52]=3)=[N:59]\[O:60][CH3:61])[C:28](=[O:29])[N:5]2[C:6]=1[C:12]([O:14][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 5928144(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acidHCID 131714150diphenylmethyl (6R,7R)-7-amino-3-bromomethyl-ceph-3-em-4-carboxylate hydrochloride

생성물 1

HCID 13579925
benzhydryl (6R,7R)-3-(bromomethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
수율 89.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

120 mg (0.24 mmol) of diphenylmethyl (6R,7R)-7-amino-3-bromomethyl-ceph-3-em-4-carboxylate hydrochloride and 120 mg (0.27 mmol) of (Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid were dissolved in 2.4 ml of methylene chloride, then 98 μl (1.2 mmol) of pyridine and 24 μl (0.27 mmol) of phosphorus oxychloride were added thereto with ice cooling, and reacted for 10 minutes. After the reaction, 12 ml of chloroform was added to the reaction mixture, which was washed with 6 ml of water twice, dried on magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (benzene-ethyl acetate (20:1)) to obtain 190 mg of the title compound.

후처리

  1. customwith ice cooling, and reacted for 10 minutes
  2. additionwas added to the reaction mixture, which
  3. washwas washed with 6 ml of water twice
  4. customdried on magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel chromatography (benzene-ethyl acetate (20:1))

출처 및 근거

ORD 기록
ord-896cbea24b5c4560bfeec950bae7e3cd
출처 데이터셋
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04785090

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