Ammonia → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 543542Notes

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.[SH:19][C:20]1[N:24]([CH3:25])[N:23]=[N:22][N:21]=1.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.N>C(#N)C.O>[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:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

Conditions

Temperature: -40 °C

Procedure

In 5.4 ml of acetonitrile were suspended 0.909 g of 7-ACA and 0.504 g of 5-mercapto-1-methyl-1H-tetrazole, and 0.256 g of water was added. The suspension was cooled at -40° C. under stirring, and 3.58 g of diphosphoryl tetrachloride was added dropwise to it at -50° to -35° C. The reaction mixture was stirred at -35° to 0° C. for 5 minutes after the dropwise addition and placed in a warm water bath at 40° C. to warm, followed by stirring at the same temperature for 20 minutes. The reaction solution was cooled over an ice water bath and, after the addition of 11 ml of cold water, it was adjusted to pH 4.0 with aqueous concentrated ammonia. The separated-out precipitate was recovered by filtration, washed with water and dried, thereby affording 0.956 g of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4 -carboxylic acid. The yield was 87.2%.

Workup

additionwas added
stirringThe reaction mixture was stirred at -35° to 0° C. for 5 minutes
additionafter the dropwise addition
customplaced in a warm water bath at 40° C.
temperatureto warm
stirringby stirring at the same temperature for 20 minutes
temperatureThe reaction solution was cooled over an ice water bath
filtrationThe separated-out precipitate was recovered by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-0c37b6a37da346a8af4bc11f1565cc12
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04446318

Reaction notes

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