Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1199758Notes

Reaction equation

S1(CCCC1)(=O)=O.C[C:9]([O:11][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.N>[Cl-].[Zn+2].[Cl-].CO.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][O:11][CH3:9])[CH2:22][S:21][C@H:16]12

Participants

Conditions

Temperature: 60 °C

Procedure

To 10 ml of sulfolane were added 2.72 g of 7-ACA, 9.0 g of zinc chloride and 1.40 g of methanol. The mixture was heated at 60° C. for 100 min to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture were added 10 ml of water and 20 ml of methanol. Then, the mixture was adjusted to pH 7.7 with aqueous ammonia at a temperature of from -2° C. to 2° C. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings. The resulting mixture was adjusted to pH 3.5 with 36 % hydrochloric acid to thereby form a precipitate. The precipitate was collected by filtration, and washed with 10 ml of cold water and, then, with 10 ml of cold methanol to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 1.02 g. The yield of the desired product was 42 %.

Workup

customa reaction
customAfter completion of the reaction
temperaturethe reaction mixture was cooled to 5° C
filtrationThe resulting precipitate was filtered off
washwashed with water
customto thereby form a precipitate
filtrationThe precipitate was collected by filtration
washwashed with 10 ml of cold water

Sources & evidence

ORD record: ord-40ba00b9edad44a9b4220ecc1a09a8b8
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04902793

Reaction notes

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