O-Cresol → HCID 10152807, compound

HRID 902663Notes

Reaction equation

HRID 902663 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].[C:32]1([CH3:39])[C:37](O)=[CH:36][CH:35]=[CH:34][CH:33]=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>[Cl:1][C:2]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:6][CH2:7][CH2:8][O:9][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH3:39]

Participants

6

Reactant 4

HCID 335O-CresolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Product 1

HCID 10152807HCID 10152807, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol (0.065 g, 0.145 mmol) in toluene (4 ml) at ambient temperature was added o-cresol (0.020 g, 0.186 mmol) under Argon with stirring. The mixture was treated with polymer bound PPh3 (0.076 g, 0.228 mmol). After 15 minutes of stirring, the mixture was treated with DIAD (0.036 g, 0.178 mmol) and was stirred at ambient temperature overnight. The reaction mixture was filtered then concentrated, in vacuo, to dryness. The oil was dissolved in DMSO and was purified via reverse-phase HPLC to yield the title compound (0.033 g, 42%); MS (ES+) m/e 539 [M+H]+.

Workup

  1. additionThe mixture was treated with polymer
  2. stirringAfter 15 minutes of stirring
  3. stirringwas stirred at ambient temperature overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationthen concentrated, in vacuo, to dryness
  6. dissolutionThe oil was dissolved in DMSO
  7. customwas purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-ab1d620af1394b4cb6ab18b156b84b9e
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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