Triphenylphosphine → Ethyl 3-(2-fluoro-4-[(4-([[2-(4-fluorophenyl)ethyl](4-isopropyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoate

HRID 732208Notes

Reaction equation

HRID 732208 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=2)[C:11]2[S:12][CH:13]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=2)=[CH:4][CH:3]=1.[F:28][C:29]1[CH:34]=[C:33](O)[CH:32]=[CH:31][C:30]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[F:28][C:29]1[CH:34]=[C:33]([O:27][CH2:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:11]3[S:12][CH:13]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=3)=[CH:25][CH:24]=2)[CH:32]=[CH:31][C:30]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 23143244(4-{[[2-(4-Fluorophenyl)ethyl](4-isopropyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol

Product 1

HCID 23143258Ethyl 3-(2-fluoro-4-[(4-([[2-(4-fluorophenyl)ethyl](4-isopropyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoateYield 64.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (4-{[[2-(4-fluorophenyl)ethyl](4-isopropyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol (510 mg), ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (280 mg), triphenylphosphine (420 mg) and diethyl azodicarboxylate (40% toluene solution, 750 mg) in toluene (3 mL) was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio) to give the title compound (490 mg, yield 64%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio)

Sources & evidence

ORD record
ord-ad9a8f184da749d993cc09b165cf5665
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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