1,2-Dichloroethane → (S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)-acetamide

HRID 1296965Notes

Reaction equation

HRID 1296965 reaction equation
Cl.[Cl:2][C:3]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][N:6]([CH2:21][C@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=1.ClCCCl.O.O[N:44]1C2C=CC=CC=2N=N1.C(N(CC)CC)C.N>ClCCl>[Cl:2][C:3]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][N:6]([CH2:21][C@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([NH2:44])=[O:19])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 68817123(S)-2-(3-{3-[(2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid hydrochloride salt

Product 1

HCID 10289382(S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (S)-2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid hydrochloride salt (50 mg, 0.1 mmol) in dichloromethane, 1,2-dichloroethane (EDC, 19.2 mg, 0.1 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 13.6 mg, 0.1 mmol), triethylamine (Et3N, 14 μl, 0.1 mmol) and ammonia (1.0M in dioxane, 0.24 ml) were added. After the resulting mixture was stirred at room temperature for over night it was washed with 0.1N HCl, saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified with HPLC to give the tittle compound as a light yellow oil 30 mg, yield 60%. MS m/e 519.0 (M+H)+.

Workup

  1. washwas washed with 0.1N HCl, saturated NaHCO3, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified with HPLC

Sources & evidence

ORD record
ord-f45395959e8946d2ba8ce60dd85908a4
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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