Water → HCID 70464043, compound

HRID 543544

Reaction equation

CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.O.[CH3:20][N:21]([CH3:31])[C:22]([CH2:24][C:25]1[S:26][C:27]([SH:30])=[N:28][N:29]=1)=[O:23].P(Cl)(Cl)(OP(Cl)(Cl)=O)=O>C(#N)C>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:30][C:27]3[S:26][C:25]([CH2:24][C:22]([N:21]([CH3:20])[CH3:31])=[O:23])=[N:29][N:28]=3)[CH2:15][S:14][C@H:9]12

Participants

Conditions

Temperature: 10 °C

Procedure

Mixed were 1.36 g of 7-ACA, 0.36 g of water and 1.32 g of 2-dimethylaminocarbonylmethyl-5-mercapto-1,3,4-thiadiazole, and 6.5 ml of acetonitrile was added. 5.04 g of diphosphoryl tetrachloride was added through a dropping funnel to the mixture at -20° to -30° C., followed by rinsing the funnel with 1.5 ml of acetonitrile. The reaction mixture was warmed at 10° C. over a period of 5 minutes with stirring, placed in a warm water bath of 40° C. and stirred at the same temperature for 20 minutes. The reaction solution was cooled with ice and adjusted to pH 4.1 with aqueous concentrated ammonia after the addition of 10 ml of cold water. The precipitate was recovered by filtration, washed with water and dried, thereby affording 1.82 g (87.6%) of 7-amino-3-(2-dimethylaminocarbonylmethyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid.

Workup

additionMixed
additionwas added
washby rinsing the funnel with 1.5 ml of acetonitrile
customplaced in a warm water bath of 40° C.
stirringstirred at the same temperature for 20 minutes
temperatureThe reaction solution was cooled with ice
additionafter the addition of 10 ml of cold water
filtrationThe precipitate was recovered by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-d0bc62e7a509467b8b3f405fab019620
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04446318

Linked notes

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