Hydrochloric Acid → HCID 131714461, compound

HRID 638086Notes

Reaction equation

HRID 638086 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][OH:34])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:20]([O:22][CH:23]([O:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:24])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[ClH:35].C(OC(C)C)(C)C>C(OCC)(=O)C.C(O)C>[ClH:35].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][OH:34])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:20]([O:22][CH:23]([O:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:24])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 131714456HCID 131714456, compound

Product 1

HCID 131714461HCID 131714461, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of DL-1-ethoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1 g) in a mixture of ethyl acetate (50 ml) and ethanol (2 ml) was added concentrated hydrochloric acid (0.3 ml) under ice-cooling, and the mixture was stirred for 10 minutes at 0°-3° C. To the solution was added diisopropyl ether (50 ml), and the resulting precipitate was collected by filtration, washed with ethyl acetate and air-dried to give DL-1-ethoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (0.8 g).

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with ethyl acetate
  4. customair-dried

Sources & evidence

ORD record
ord-12ccffdd0e244499a872fb7b22e57040
Source dataset
uspto-grants-1985_12
Patent number
US04559334

Reaction notes

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