2-Dimethylaminopyridine → HCID 9937985, compound

HRID 1635085Notes

Reaction equation

HRID 1635085 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH:10]([C:14]([O:27][CH2:28][CH2:29][NH2:30])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([OH:13])=[O:12])[N:3]=1.C(N(C(C)C)C(C)C)C.CN(C1C=CC=CN=1)C.[CH3:49][O:50][C:51]1[CH:52]=[C:53]([CH:57]=[CH:58][C:59]=1[O:60][CH3:61])[C:54](Cl)=[O:55]>C(Cl)Cl.C(OCC)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH:10]([C:14]([O:27][CH2:28][CH2:29][NH:30][C:54](=[O:55])[C:53]2[CH:57]=[CH:58][C:59]([O:60][CH3:61])=[C:51]([O:50][CH3:49])[CH:52]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([OH:13])=[O:12])[N:3]=1

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 77070Veratroyl chlorideHCID 81531DiisopropylethylamineHCID 18675632HCID 18675632, compound

Product 1

HCID 9937985HCID 9937985, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (2.5 mmol) of 2-(4,6-dimethylpyrimidin-2-yloxy)-3-(2-aminoethoxy)-3,3-diphenylpropionic acid in 10 ml of methylene chloride was successively admixed at room temperature with 0.35 g (2.7 mmol) of N-ethyldiisopropylamine, 0.03 g (0.2 mmol) of dimethylaminopyridine and 0.54 g (2.7 mmol) of 3,4-dimethoxybenzoyl chloride. The mixture was stirred at room temperature for 4 days and then diluted with diethyl ether and extracted with 1M hydrochloric acid and 1M aqueous sodium hydroxide solution, and the combined alkaline phases were made acidic and extracted with ether. The organic phase was dried over sodium sulfate, the solvent was distilled off and the residue (0.9 g) was chromatographed over silica gel (methylene chloride/methanol 9:1). Yield: 280 mg of a white foam.

Workup

  1. extractionextracted with 1M hydrochloric acid and 1M aqueous sodium hydroxide solution
  2. extractionextracted with ether
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. distillationthe solvent was distilled off
  5. customthe residue (0.9 g) was chromatographed over silica gel (methylene chloride/methanol 9:1)

Sources & evidence

ORD record
ord-c5527819272848a7a94fbf70f3fcaa20
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

Loading…