1,2-Dichloroethane → N-((1R)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-{4-[2-(trifluoromethyl}phenyl]-piperidyl)ethyl)(tert-butoxy)carboxamide

HRID 489670Notes

Reaction equation

HRID 489670 reaction equation
Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.[NH:27]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:28]([C:37](O)=[O:38])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][C@@H:28]([NH:27][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:37](=[O:38])[N:13]2[CH2:12][CH2:11][CH:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([F:2])([F:16])[F:17])[CH2:15][CH2:14]2)=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 219369704-[2-(Trifluoromethyl)phenyl]piperidine hydrochloride

Product 1

HCID 69151295N-((1R)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-{4-[2-(trifluoromethyl}phenyl]-piperidyl)ethyl)(tert-butoxy)carboxamideYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1 (Step f) from 4-[2-(trifluoromethyl)phenyl]piperidine hydrochloride (Step c) (0.792 g, 3.0 mmol), DIEA (0.54 mL, 3.0 mmol), Boc-p-Cl-D-PheOH (PepTech Corporation) (1.36 g, 4.5 mmol), HOAT (Aldrich) (0.615 g, 4.5 mmol) and EDC (Aldrich) (0.864 g, 4.5 mmol) in DMF (5 mL). Purification by silica gel chromatography (5:2 hexane:EtOAc) provided the title compound as a white foam (1.06 g). MS (ESI, pos. ion) m/z: 511 (M+1); MS (ESI, neg. ion) m/z: 509 (M−1). Calc'd for C26H30ClF3N2O3: 510.98.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (5:2 hexane:EtOAc)

Sources & evidence

ORD record
ord-afbfe84470df4dedb5f4851b93aac868
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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