Hydrochloric Acid → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 1979618Notes

Reaction equation

[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.CC(O[CH2:12][C:13]1[CH2:22][S:21][C@@H:16]2[C@H:17]([NH2:20])[C:18](=[O:19])[N:15]2[C:14]=1[C:23]([OH:25])=[O:24])=O.Cl>C(N(CC)CC)C.O>[NH2:20][CH:17]1[C:18](=[O:19])[N:15]2[C:14]([C:23]([OH:25])=[O:24])=[C:13]([CH2:12][S:7][C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)[CH2:22][S:21][C@H:16]12

Participants

Conditions

Temperature: 53 °C

Procedure

A solution of 72.5 g of 1-methyl-5-mercapto-1,2,3,4-tetrazole (MTA) in 87.5 ml of triethylamine in 3 liters of water was heated to 75° C. 68 g of 7-aminocephalosporanic acid (92%) were added, to give a suspension with pH 4.35. 28 ml of triethylamine were added at the same temperature and the solution thus formed, with pH 5.20, was held for 30 min at 75° C. and 60 min at 53° C. Throughout the whole operation the reaction isoelectric pH was held to 5.25 with the gradual addition of a solution of 20 g of thiol (MTA) in 175 ml of water. The formation rate of the precipitate increased on cooling to 53° C. The mixture was adjusted to pH 4.25 at 25° C. with concentrated hydrochloric acid. It was filtered, washed with water and then acetone to give 52.8 g of the compound of the title with a 70% yield. It was recrystallised out of an aqueous hydrochloric acid solution at pH 2.20 and isolated with a m.p. 224° C. (d).

Workup

customto give a suspension with pH 4.35
customthe solution thus formed, with pH 5.20
temperatureThe formation rate of the precipitate increased
filtrationIt was filtered
washwashed with water

Sources & evidence

ORD record: ord-51348d57f6394657a88ada2d730ff7b4
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04481357

Reaction notes

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