Hydrochloric Acid → HCID 131712598, compound

HRID 1659772Notes

Reaction equation

HRID 1659772 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[N:35]=[C:36]([NH:39]C=O)[S:37][CH:38]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([OH:31])=[O:30])=[C:19]([CH2:22][S:23][C:24]3[S:25][CH:26]=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[N:35]=[C:36]([NH2:39])[S:37][CH:38]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([OH:31])=[O:30])=[C:19]([CH2:22][S:23][C:24]3[S:25][CH:26]=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712596HCID 131712596, compound

Product 1

HCID 131712598HCID 131712598, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-t-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.3 g.), conc. hydrochloric acid (3.74 g.) and methanol (35 ml.) was stirred for 2 hours and 40 minutes at ambient temperature. The solvent was distilled off under reduced pressure and the residue was dissolved in a 10% aqueous solution of sodium hydroxide (pH 7~8). The aqueous solution was adjusted to pH 3.0 with 10% hydrochloric acid under ice-cooling and stirring and stirred for 30 minutes. Precipitates were collected by filtration, washed with water and dried to give 7-[2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in a 10% aqueous solution of sodium hydroxide (pH 7~8)
  3. temperaturecooling
  4. stirringstirring
  5. stirringstirred for 30 minutes
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-71270fed343c447c9900af55aafeef8c
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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