Tributylphosphine → 3-(4-{1-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentyloxy}-benzoylamino)-propionic acid methyl ester

HRID 1669301Notes

Reaction equation

HRID 1669301 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[F:17][C:18]([F:38])([F:37])[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:31](O)[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:27][CH:26]=2)=[N:23][CH:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:31]([C:28]2[CH:27]=[CH:26][C:25]([C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:38])([F:17])[F:37])=[CH:24][N:23]=3)=[CH:30][CH:29]=2)[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 673422541-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol

Product 1

HCID 673432223-(4-{1-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentyloxy}-benzoylamino)-propionic acid methyl esterYield 48.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (232 mg, 1.04 mmol) and 1-[4-(5-trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol (258 mg, 0.830 mmol) in toluene (5.0 mL) is degassed and filled with nitrogen for 3 times. Tributyl-phosphine (0.310 mL, 1.50 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (316 mg, 1.50 mmol). The reaction mixture is allowed to warm to room temperature and stirred over night, the mixture is loaded on silica gel column. The 3-(4-{1-[4-(5-trifluoromethyl-pyridin-2-yl)-phenyl]-pentyloxy}-benzoylamino)-propionic acid methyl ester (205 mg, 0.40 mmol), 47%, is obtained in purified form after flash column chromatography.

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-45cd7a2c638f4b73ac76ff5874a1bbb7
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…