Methylparaben → HCID 69416683, compound

HRID 1296974Notes

Reaction equation

HRID 1296974 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][C:38]([O:25][CH2:24][CH2:23][CH2:22][N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[C:12]=2[Cl:21])[CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Product 1

HCID 69416683HCID 69416683, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(2,2-diphenylethyl)-N-(3-hydroxy-propyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (0.60 g, 1.33 mmol) in toluene (4 ml) at ambient temperature was added 4-hydroxy-benzoic acid methyl ester (0.22 g, 1.45 mmol) under Argon with stirring. The mixture was treated with polymer bound PPh3 (0.71 g, 2.13 mmol). After 15 minutes of stirring the mixture was treated with DIAD (0.32 mL, 1.66 mmol) and was stirred at room temperature overnight. The reaction mixture was filtered, and concentrated in-vacuo. The resulting oil was dissolved in DMSO and was purified via preparative reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to yield the title compound, 0.24 g (32%); MS (ESI) m/e 583 [M+H]+.

Workup

  1. additionThe mixture was treated with polymer
  2. stirringAfter 15 minutes of stirring the mixture
  3. stirringwas stirred at room temperature overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in-vacuo
  6. dissolutionThe resulting oil was dissolved in DMSO
  7. customwas purified via preparative reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

Sources & evidence

ORD record
ord-e2a326f1c84c43fab62dd2a6959c0f5c
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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