Methanol → 2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

HRID 851585Notes

Reaction equation

HRID 851585 reaction equation
N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:8].[CH3:13][CH:14]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[N:17]2[C:28](=[O:40])[CH:29]([NH:30]C(=O)CC3C=CC=CC=3)[C@H:16]2[S:15]1.CO>ClCCl>[ClH:8].[CH3:13][CH:14]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:25])[Cl:26])=[O:21])[N:17]2[C:28](=[O:40])[CH:29]([NH2:30])[C@H:16]2[S:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 705273932,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.55 g.) and phosphorus pentachloride (1.43 g.) were added in turn under cooling at -5° to -10° C. to a suspension of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (2.14) in dried dichloromethane (20 ml.), and the mixture was stirred. After dissolution of the starting material, the reaction temperature was elevated to at room temperature, and stirred for 4 hours. To this solution was dropwise added absolute methanol (1.47 g.) under cooling at -10° to -15° C. After stirring for 1 hour at the same temperature and 1.5 hours at 2° to 3° C., the precipitated crystals were collected by filtration, washed with a small amount of dichloromethane and ether, and dried to give colorless crystals of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (1.26 g.), mp 185° to 187° C. (dec.). Similar results were obtained by using the following compounds as a starting compound instead of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate.

Workup

  1. dissolutionAfter dissolution of the starting material
  2. customwas elevated to at room temperature
  3. stirringstirred for 4 hours
  4. temperatureunder cooling at -10° to -15° C
  5. stirringAfter stirring for 1 hour at the same temperature and 1.5 hours at 2° to 3° C.
  6. filtrationthe precipitated crystals were collected by filtration
  7. washwashed with a small amount of dichloromethane and ether
  8. customdried

Sources & evidence

ORD record
ord-c71688b6f9d44c27826ef950579b1169
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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