Pyridine → 2,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

HRID 436465Notes

Reaction equation

HRID 436465 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[C:15]([CH3:19])([CH3:18])[S:16](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[ClH:36].N1C=CC=CC=1>ClC(Cl)CCl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[C:15]([CH3:19])([CH2:18][Cl:36])[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10176127Pyridinium chlorideHCID 122939442,2,2-Trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide

Product 1

HCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylateYield 17.3%

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3- carboxylate-1-oxide (0.96 g.) was dissolved in 1,1,2-trichloroethane (15 cc ), and pyridine (0.32 g.) and pyridine hydrochloride (0.12 g.) were added thereto. The mixture was heated at 100° C., for 3 hours, cooled, washed with water, dried and then concentrated. The residue was subjected to a chromatography of silica gel in which chloroform was used as the eluant. The eluate was concentrated to yield, as the residue, crystals (0.09 g.) of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2- methyl-2-chloromethylpenam-3-carboxylate, m.p. 104° - 105° C.

Workup

  1. temperaturecooled
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-ba5a82db951c4522857db72b3a4843b0
Source dataset
uspto-grants-1977_02
Patent number
US04009159

Reaction notes

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