Ammonia → 7-Amino-3-(2-ethoxycarbonylmethylthio-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 543535

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.[CH2:19]([O:21][C:22]([CH2:24][S:25][C:26]1[S:27][C:28]([SH:31])=[N:29][N:30]=1)=[O:23])[CH3:20].COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O.N>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:31][C:28]3[S:27][C:26]([S:25][CH2:24][C:22]([O:21][CH2:19][CH3:20])=[O:23])=[N:30][N:29]=3)[CH2:15][S:14][C@H:9]12

Participants

Conditions

Temperature: 40 °C

Procedure

A 8.0 ml portion of acetonitrile was added to 1.36 g of 7-ACA and 1.54 g of 2-ethoxycarbonylmethylthio-5-mercapto-1,3,4-thiadiazole, and the mixture was cooled to -40° to -30° C., followed by adding thereto dropwise 5.40 g of DCPA under stirring. The external bath was removed and the reaction mixture was stirred for 8 minutes, then warmed at 40° C. and stirred for 20 minutes to allow the reaction to proceed. The reaction solution was poured into 10 ml of ice-water, which was adjusted to pH 4.4 with 25% aqueous ammonia. The precipitated powder was recovered by filtration, washed with water and dried, thereby affording 2.08 g (92.7% of yield) of 7-amino-3-[(2-ethoxycarbonylmethylthio-1,3,4-thiadiazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid in the form of mud yellow powder.

Workup

temperaturethe mixture was cooled to -40° to -30° C.
additionby adding
customThe external bath was removed
stirringstirred for 20 minutes
customthe reaction
filtrationThe precipitated powder was recovered by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-b2f8e05831e84f959441fcce510434c4
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04446318

Linked notes

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