Triphenylphosphine → 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester hydrochloride salt

HRID 229115Notes

Reaction equation

HRID 229115 reaction equation
[Cl:1][C:2]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][OH:9].[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37](O)[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[ClH:1].[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:2]=2[Cl:1])[CH2:10][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Product 1

HCID 688654923-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester hydrochloride saltYield 60.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propan-1-ol (0.60 g, 1.34 mmol) in toluene (4 mL) at RT was added 3-hydroxy-benzoic acid methyl ester (0.22 g, 1.45 mmol). The mixture was treated with polymer bound triphenylphosphine (0.82 g, 2.50 mmol, 3 mmol/g, Fluka Chemie) (0.71 g, 2.14 mmol, 3 mmol/g, Fluka Chemie). After 15 minutes of stirring, the mixture was treated with DIAD (0.33 mL, 1.67 mmol) and was stirred overnight at RT. The reaction mixture was filtered, concentrated and purified via preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to yield the title compound (0.25 g, 32%); MS (ES+) m/e 583 [M+H]+.

Workup

  1. additionThe mixture was treated with polymer
  2. stirringwas stirred overnight at RT
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. custompurified via preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

Sources & evidence

ORD record
ord-79c78efefef843af88d2ffd62ceb66a8
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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