7-Aminocephalosporanic acid → 7-Amino-3-(5-acetamidomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1395771Notes

Reaction equation

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]([NH:22][CH2:23][C:24]1[S:28][C:27]([SH:29])=[N:26][N:25]=1)(=[O:21])[CH3:20].C(=O)(O)[O-].[Na+]>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:27]3[S:28][C:24]([CH2:23][NH:22][C:19](=[O:21])[CH3:20])=[N:25][N:26]=3)[CH2:15][S:14][C@H:9]12

Participants

Conditions

Temperature: 60 °C

Procedure

7-Aminocephalosporanic acid (1.36 g.), 5-acetamidomethyl-1,3,4-thiadiazole-2-thiol (1.04 g.) and sodium bicarbonate (885 mg.) were dissolved in water (70 ml.), and the solution was stirred at 60° C. for 5 hrs. After the reaction, the reaction mixture was adjusted to pH 5, and then allowed to stand overnight in a refrigerator. The precipitating crystals were collected by filtration to give 7-amino-3-(5-acetamidomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.03 g.) m.p. 195°-197° C. (dec.).

Workup

customAfter the reaction
waitto stand overnight in a refrigerator
filtrationThe precipitating crystals were collected by filtration

Sources & evidence

ORD record: ord-7619ab005afd4121b39cae253a0bb949
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04205166

Reaction notes

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