Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
Reaction equation
[N+](C)([O-])=O.C[C:6]([O:8][CH2:9][C:10]1[CH2:19][S:18][C@@H:13]2[C@H:14]([NH2:17])[C:15](=[O:16])[N:12]2[C:11]=1[C:20]([OH:22])=[O:21])=O.B(F)(F)F.N>[Cl-].[Zn+2].[Cl-].CO.O>[NH2:17][CH:14]1[C:15](=[O:16])[N:12]2[C:11]([C:20]([OH:22])=[O:21])=[C:10]([CH2:9][O:8][CH3:6])[CH2:19][S:18][C@H:13]12Participants
Conditions
- Temperature
- 60 °C
Procedure
To 10 ml of nitromethane were added 3.0 g of 7-ACA, 10.0 g of zinc chloride and 3.9 g of a complex of boron trifluoride with methanol (boron trifluoride content: 51%). The mixture was heated at 60° C. for 20 min to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture were added 30 ml of water and 5 ml of methanol. Then, the mixture was adjusted to pH 8.0 with 28% aqueous ammonia at a temperature of -5° 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 20 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 1.4 g. The yield of the desired product was 52%.
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-bc48c4182d1e436a905c7f3ddc8ad6cc
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902793
Reaction notes
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