Hydrochloric Acid → HCID 68140931, compound

HRID 1729670Notes

Reaction equation

HRID 1729670 reaction equation
C(C=C([NH:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C@@H:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C@@:14]([Cl:18])([CH3:17])[CH2:15][S:16][C@H:11]12)C)(OCC)=O.Cl>C(Cl)(Cl)Cl.CC(C)=O>[NH2:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C@@H:13]([C:19]([O:21][CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])[C@@:14]([Cl:18])([CH3:17])[CH2:15][S:16][C@H:11]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86734115HCID 86734115, compound

Product 1

HCID 68140931HCID 68140931, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

A solution of benzhydryl 7β-(1-carbethoxy-1-propen-2-ylamino)-3β-chloro-3α-methylcepham-4α-carboxylate (107 mg) and 1N hydrochloric acid (0.1 ml) in a mixture of chloroform and acetone (1:1; 2 ml) is stirred at room temperature for 1 hour. The reaction mixture is washed with water, dried, and evaporated to remove the solvent. The residue is treated with a mixture of ether and petroleum ether to give solid benzhydryl 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylate (60 mg).

Workup

  1. washThe reaction mixture is washed with water
  2. customdried
  3. customevaporated
  4. customto remove the solvent
  5. additionThe residue is treated with a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-a86514a70bfd42d8a22d778220112bca
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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