Hydrochloric Acid → HCID 131712546, compound

HRID 1155173Notes

Reaction equation

HRID 1155173 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:29])[CH:12]([NH:13][C:14](=[O:28])[C:15](=[N:24][O:25][CH2:26][CH3:27])[C:16]3[N:17]=[C:18]([NH:21]C=O)[S:19][CH:20]=3)[C@H:4]2[S:3]1.[ClH:30]>CO>[ClH:30].[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:29])[CH:12]([NH:13][C:14](=[O:28])[C:15](=[N:24][O:25][CH2:26][CH3:27])[C:16]3[N:17]=[C:18]([NH2:21])[S:19][CH:20]=3)[C@H:4]2[S:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 131712545HCID 131712545, compoundHCID 178474896HCID 178474896, compound

Product 1

HCID 131712546HCID 131712546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-methyl-7-[2-ethoxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-ethoxyimino-2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (3.0 g) in methanol (40 ml) was cooled in an ice-water bath and thereto was added dropwise a solution of concentrated hydrochloric acid (3.8 g) in methanol (12 ml) with stirring and then stirring was continued at room temperature. After 35 minutes stirring a homogeneous solution was formed and then 2 hours later precipitates appeared and thereafter diethyl ether (300 ml) was added thereto. The precipitates were collected by filtration, washed with diethyl ether and then dried over phosphorus pentoxide under reduced pressure to give powder of 2-methyl-7-[2-ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid hydrochloride (syn isomer), which can be represented as 2-methyl-7-[2-ethoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid hydrochloride (syn isomer), (2.6 g).

Workup

  1. temperaturewas cooled in an ice-water bath
  2. stirringstirring
  3. customwas continued at room temperature
  4. stirringAfter 35 minutes stirring a homogeneous solution
  5. customwas formed
  6. custom2 hours later precipitates
  7. additiondiethyl ether (300 ml) was added
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with diethyl ether
  10. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-f1ba60cb717c4f89996f0faaf80e5527
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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