Triethylamine → Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide

HRID 615414Notes

Reaction equation

HRID 615414 reaction equation
[SH:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:51]1[N:52]=[CH:53][S:54][CH:55]=1)[C:20]([NH:22][CH:23]1[C:49](=[O:50])[N:25]2[C:26]([C:33]([O:35][CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[C:27]([CH2:31]Cl)[CH2:28][S:29](=[O:30])[C@H:24]12)=[O:21])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.O>[C:9]([O:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:51]1[N:52]=[CH:53][S:54][CH:55]=1)[C:20]([NH:22][CH:23]1[C:49](=[O:50])[N:25]2[C:26]([C:33]([O:35][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[O:34])=[C:27]([CH2:31][S:1][C:2]3[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=3)[CH2:28][S:29](=[O:30])[C@H:24]12)=[O:21])=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 131714108Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxideHCID 1784272856-Methylpyridazine-3-thiol

Product 1

HCID 131714107Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxideYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Mercapto-6-methylpyridazine (1 g) was added to a mixture of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (5.0 g) in N,N-dimethylformamide (25 ml) and triethylamine (0.7 g) under ice-cooling and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (4.8 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5a38c86ebe254558a4def108524ed1b8
Source dataset
uspto-grants-1985_02
Patent number
US04499088

Reaction notes

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