Trifluoroacetic acid → 3-Methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid
Reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:46])[C:17]([C:21]3[N:22]=[C:23]([NH:26]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:24][CH:25]=3)=[N:18][O:19][CH3:20])[C:13](=[O:47])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11].FC(F)(F)C(O)=O>>[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:46])[C:17]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)=[N:18][O:19][CH3:20])[C:13](=[O:47])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11]Participants
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 6.15 g of the product of Step A and 61 ml of trifluoroacetic acid was stirred at 20° C. for 20 minutes and the mixture was evaporated under reduced pressure at 30° C. to a volume of 15 ml. 150 ml of ispropyl ether were added at 10° C. to the mixture which was then stirred at 20° C. for 15 minutes and was vacuum filtered. The 3.2 g of raw product were chromatographed over silica gel and were eluted with aqueous 2M sodium chloride solution containing 4% of 1M sodium bicarbonate solution. The raw product was dissolved in a mixture of 10 ml of eluant, 1.4 ml of aqueous 1M sodium bicarbonate solution, 1 ml of triethylamine and 1 ml of aqueous saturated sodium chloride solution and the solution was acidified to a pH of 3 by addition of 50% aqueous formic acid. The mixture was vacuum filtered and the product was washed with water and then with ether to obtain 0.99 g of syn isomer of 3-methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.
Workup
- customthe mixture was evaporated under reduced pressure at 30° C. to a volume of 15 ml
- addition150 ml of ispropyl ether were added at 10° C. to the mixture which
- stirringwas then stirred at 20° C. for 15 minutes
- filtrationfiltered
- customThe 3.2 g of raw product were chromatographed over silica gel
- washwere eluted with aqueous 2M sodium chloride solution
- additioncontaining 4% of 1M sodium bicarbonate solution
- dissolutionThe raw product was dissolved in a mixture of 10 ml of eluant, 1.4 ml of aqueous 1M sodium bicarbonate solution, 1 ml of triethylamine and 1 ml of aqueous saturated sodium chloride solution
- additionthe solution was acidified to a pH of 3 by addition of 50% aqueous formic acid
- filtrationfiltered
- washthe product was washed with water
Sources & evidence
- ORD record
- ord-7f0104aae5994c74944c63218e03f4a3
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04992431
Reaction notes
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