Pyridine → HCID 131711023, compound

HRID 2106929Notes

Reaction equation

HRID 2106929 reaction equation
ClC(Cl)(Cl)[CH2:3][O:4][C:5]([N:7]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:8][C:9]([NH:11][CH:12]1[C:29](=[O:30])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22])[C:16]([CH3:20])([CH2:18]Br)[S:17][C@H:13]12)=[O:10])=[O:6].N1C=CC=CC=1.[CH:45]([Cl:48])([Cl:47])[Cl:46]>>[Cl:46][C:45]([Cl:48])([Cl:47])[CH2:3][O:4][C:5]([N:7]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:8][C:9]([NH:11][CH:12]1[C:29](=[O:30])[N:14]2[C:15]([C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:26])[Cl:27])=[O:22])=[C:16]([CH3:18])[CH2:20][S:17][C@H:13]12)=[O:10])=[O:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 6212ChloroformHCID 88606570HCID 88606570, compound

Product 1

HCID 131711023HCID 131711023, compound

Procedure

A mixture of 2,2,2-trichloroethyl 6-[N-(2,2,2-trichloroethoxycarbonyl)phenylglycyl]amino-2-methyl-2-bromomethylpenam-3-carboxylate (0.43 g.), dry pyridine (0.09 g.) and dry chloroform (10 cc) was heated under reflux for 4.5 hours. The chloroform layer was separated, washed with water, dried and then concentrated. The residue was recrystallized from ether to yield needles (0.23 g.) of 2,2,2-trichloroethyl 7-[N-(2,2,2-trichloroethoxycarbonyl)phenylglycyl]amino-3-methyl-3-cephem-4-carboxylate, m.p. 99°-100.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 hours
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-fd496125f5e94790b63d478814c91c19
Source dataset
uspto-grants-1990_06
Patent number
US04931555

Reaction notes

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