Pyridine → HCID 131711023, compound

HRID 647776Notes

Reaction equation

HRID 647776 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-516934c05f0b4efcbbede91945b8ce10
Source dataset
uspto-grants-1983_10
Patent number
US04410458

Reaction notes

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