Hydrochloric Acid → HCID 131712740, compound
Reaction equation
[ClH:1].[CH:2]1([O:7][N:8]=[C:9]([C:32]2[N:33]=[C:34]([NH:37]C=O)[S:35][CH:36]=2)[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3]1>CO>[ClH:1].[CH:2]1([O:7][N:8]=[C:9]([C:32]2[N:33]=[C:34]([NH2:37])[S:35][CH:36]=2)[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Conc. hydrochloric acid (1.8 g) was added to a solution of 7-[2-cyclopentyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.7 g) in methanol (27 ml) and the mixture was stirred for 2 hours at ambient temperature. An insoluble material was filtered off and the filtrate was concentrated to dryness under reduced pressure and the residue was triturated with diethyl ether and dried to give 7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer) (2.9 g). The powder (2.9 g) was dissolved in an aqueous solution of sodium hydroxide to adjust pH 7.5. The solution was adjusted to pH 3.0 and precipitates were collected by filtration and washed with water to give 7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.95 g).
Workup
- filtrationAn insoluble material was filtered off
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- customthe residue was triturated with diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-0c69ef9560374334a3060c3944579ab4
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04331664
Reaction notes
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