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 2231989Notes

Reaction equation

HRID 2231989 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 13579925benzhydryl (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-carboxylateYield 89.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-896cbea24b5c4560bfeec950bae7e3cd
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

Loading…