2-Dimethylaminopyridine → HCID 70074289, compound

HRID 1939654Notes

Reaction equation

HRID 1939654 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:7]([C:18]([O-])=[O:19])=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][C:10]=1[CH3:11])=[O:4].CN(C1C=CC=CN=1)C.[C:39]([O:43][C:44](=[O:47])[CH2:45][NH2:46])([CH3:42])([CH3:41])[CH3:40]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:7]([C:18]([NH:46][CH2:45][C:44]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:47])=[O:19])=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 151417Glycine tert-butyl esterHCID 70074118HCID 70074118, compound

Product 1

HCID 70074289HCID 70074289, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

More specifically, a dried methylene chloride solution containing 394 mg (1 mmol) of 1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyridine-3-carboxylate, 309 mg (1.5 mmol) of dicyctohexylcarbodiimide and 134 mg (1.1 mmol) of dimethylaminopyridine was stirred for one hour. To this reaction mixture, 157 mg (1.2 mmol) of glycine t-butyl ester was added and the reaction mixture was refluxed for 2 hours. Insoluble components were removed from the reaction mixture by filtration and the reaction mixture was chromatographed on a silica gel column for purification, whereby 508 mg (100%) of the captioned compound was obtained as an oily material.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customInsoluble components were removed from the reaction mixture by filtration
  3. customthe reaction mixture was chromatographed on a silica gel column for purification

Sources & evidence

ORD record
ord-27c82001964f46cd836a7034eeaf44bb
Source dataset
uspto-grants-1997_12
Patent number
US05696268

Reaction notes

Loading…