Sulfuric Acid → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
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.S(=O)(=O)(O)O.B(OC)(OC)OC.S([O-])([O-])(=O)=S.[Na+].[Na+]>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]12Participants
Conditions
- Temperature
- 30 °C
Procedure
To 20 ml of sulfolane were added 1.41 g of 7-ACA, 1.96 g of ferric chloride, 0.29 ml of concentrated sulfuric acid and 1.22 ml of trimethyl borate. The mixture was heated at 30° C. for 3 hours to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 0° C. To the reaction mixture were added 30 ml of water, 10 ml of methanol and 3.04 g of sodium thiosulfate and the mixture was stirred for 1 hour while cooling with ice. The resultant precipitate was filtered off, and then washed with methanol. The filtrate was combined with the washings. The resultant 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 20 ml of cold methanol, to thereby obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 1.05 g. The yield of the desired product was 83%.
Workup
- customa reaction
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to 0° C
- temperaturewhile cooling with ice
- filtrationThe resultant precipitate was filtered off
- washwashed with methanol
- customto thereby form a precipitate
- filtrationThe precipitate was collected by filtration
- washwashed with 10 ml of cold water
Sources & evidence
- ORD record
- ord-1b4ddd3489a24d83a01223f45bd9ca3d
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05034521
Reaction notes
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