Hydrochloric Acid → 3-[(8-Amino-6-tetrazolo[1,5-b]pyridazinyl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1065847Notes

Reaction equation

C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:29])[C:19]([C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:30])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.C([O-])(O)=O.[Na+].[NH2:36][C:37]1[C:38]2[N:39]([N:44]=[N:45][N:46]=2)[N:40]=[C:41]([SH:43])[CH:42]=1.Cl>O>[NH2:36][C:37]1[C:38]2[N:39]([N:44]=[N:45][N:46]=2)[N:40]=[C:41]([S:43][CH2:5][C:6]2[CH2:7][S:8][C@@H:9]3[CH:16]([NH:17][C:18](=[O:29])[C:19]([C:23]4[N:24]=[C:25]([NH2:28])[S:26][CH:27]=4)=[N:20][O:21][CH3:22])[C:15](=[O:30])[N:10]3[C:11]=2[C:12]([OH:14])=[O:13])[CH:42]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn-isomer), (0.456 g, 0.001 mole) and NaHCO3 (0.143 g, 0.0017 mole) in water (10 ml), 8-amino-6-mercapto-tetrazolo[1,5-b]pyridazine (0.118 g, 0.0007 mole) was added. A slow stream of nitrogen was passed through the solution, and the mixture was heated at 50° C. for 12 hours, while keeping the pH at 6.8. After cooling, the solution was acidified with 10% HCl, the precipitate collected by filtration, washed with water and then with ethanol. There was thus obtained 0.215 g of compound (2) which was shown by NMR, TLC and IR, to be identical to the product described in Example 1, apart a minor contaminant of the anti-isomer. By using the same method, the following compounds were prepared:

Workup

temperatureAfter cooling
filtrationthe precipitate collected by filtration
washwashed with water
customthe following compounds were prepared

Sources & evidence

ORD record: ord-6d1498a2de0e4a1ca3435f7ae2834f24
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04331666

Reaction notes

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