Hydrochloric Acid → 7-[2-Methylthiomethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 2412776Notes

Reaction equation

HRID 2412776 reaction equation
CO[S:3][CH2:4][O:5][N:6]=[C:7]([C:30]1[N:31]=[C:32]([NH:35]C=O)[S:33][CH:34]=1)[C:8]([NH:10][CH:11]1[C:28](=[O:29])[N:13]2[C:14]([C:25]([OH:27])=[O:26])=[C:15]([CH2:18][S:19][C:20]3[S:21][CH:22]=[N:23][N:24]=3)[CH2:16][S:17][C@H:12]12)=[O:9].Cl.[CH3:39]O>O1CCCC1>[CH3:39][S:3][CH2:4][O:5][N:6]=[C:7]([C:30]1[N:31]=[C:32]([NH2:35])[S:33][CH:34]=1)[C:8]([NH:10][CH:11]1[C:28](=[O:29])[N:13]2[C:14]([C:25]([OH:27])=[O:26])=[C:15]([CH2:18][S:19][C:20]3[S:21][CH:22]=[N:23][N:24]=3)[CH2:16][S:17][C@H:12]12)=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131714083HCID 131714083, compound

Product 1

HCID 1317125977-[2-Methylthiomethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-methoxythiomethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.58 g.), conc. hydrochloric acid (0.405 g.), methanol (8.7 ml.) and tetrahydrofuran (5 ml.) was stirred for 2 hours and 10 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 7~8.5). An insoluble material was filtered off and the filtrate was adjusted to pH 3.4 with 10% hydrochloric acid under ice-cooling and stirred for 30 minutes. Precipitates were collected by filtration, washed with water and dried to give 7-[2-methylthiomethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.4 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 7~8.5)
  3. filtrationAn insoluble material was filtered off
  4. temperaturecooling
  5. stirringstirred for 30 minutes
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-cd0b3423cd064c038efcd39c68f76447
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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