Triethylamine → HCID 58859135, compound

HRID 1349471Notes

Reaction equation

HRID 1349471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:30][CH:31]([O:34][CH3:35])[O:32][CH3:33])[CH:11]=[C:12]([CH:24]([OH:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:30][CH:31]([O:34][CH3:35])[O:32][CH3:33])[CH:11]=[C:12]([C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 58859156HCID 58859156, compound

Product 1

HCID 58859135HCID 58859135, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-(1-hydroxy-2,2-dimethylpropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (120 mg) obtained in Example 118, Step 2 in dimethyl sulfoxide (5 ml) were added triethylamine (1.1 ml) and sulfur trioxide pyridine complex (450 mg) and the mixture was stirred at room temperature for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted twice with ethyl acetate (30 ml). The combined ethyl acetate layer washed with water, dried, concentrated and purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-(2,2-dimethylpropionyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (104 mg).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate (30 ml)
  2. washThe combined ethyl acetate layer washed with water
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-a27bdbbd42b545d496fe0865b2eab9a8
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

Loading…