Hydrochloric Acid → HCID 131712549, compound

HRID 1155175Notes

Reaction equation

HRID 1155175 reaction equation
CO.[CH3:3][CH:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]2[C:13](=[O:32])[CH:14]([NH:15][C:16](=[O:31])[C:17](=[N:26][O:27][CH:28]([CH3:30])[CH3:29])[C:18]3[N:19]=[C:20]([NH:23]C=O)[S:21][CH:22]=3)[C@H:6]2[S:5]1.Cl>O1CCCC1>[CH3:3][CH:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]2[C:13](=[O:32])[CH:14]([NH:15][C:16](=[O:31])[C:17](=[N:26][O:27][CH:28]([CH3:29])[CH3:30])[C:18]3[N:19]=[C:20]([NH2:23])[S:21][CH:22]=3)[C@H:6]2[S:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131712548HCID 131712548, compoundHCID 178460194HCID 178460194, compound

Product 1

HCID 131712549HCID 131712549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methanol (13 ml) and tetrahydrofuran (13 ml) was dissolved 2-methyl-7-[2-isopropoxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-isopropoxyimino-2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (1.7 g) and thereto was added concentrated hydrochloric acid (1.5 ml) with stirring at room temperature and then stirring was continued for 2 hours at room temperature. The reaction mixture was concentrated to dryness and the solid was dissolved in water (100 ml) by adding sodium bicarbonate, whereby the resulting mixture was adjusted to pH 7.0. The solution was adjusted to pH 3.0 with concentrated hydrochloric acid under ice-cooling. Precipitates were collected by filtration, washed with water and then dried to give 2-methyl-7-[2-isopropoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-isopropoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (1.2 g).

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe solid was dissolved in water (100 ml)
  4. additionby adding sodium bicarbonate, whereby the resulting mixture
  5. temperaturecooling
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-f94b191ca58e425a811e6403ba82fb9b
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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