Trifluoroacetic acid → (2R, 5S)-2-[4-Chloro-2-(piperazine-1-carbonyl)-phenoxy]-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 480183Notes

Reaction equation

HRID 480183 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:42])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH2:23][C:24]([N:26]2[CH2:31][C@H:30]([CH3:32])[N:29]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:28][C@H:27]2[CH3:41])=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClC(Cl)C.ClCCl>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH2:23][C:24]([N:26]2[CH2:31][C@H:30]([CH3:32])[N:29]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:28][C@H:27]2[CH3:41])=[O:25])=[C:15]([C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:42])[CH:20]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12112117(2R, 5S)-4-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 9935847(2R, 5S)-2-[4-Chloro-2-(piperazine-1-carbonyl)-phenoxy]-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 87.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (2R, 5S)-4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (0.110 g, 0.182 mmol) in dichloroethane (10 ml) was added trifluoroacetic acid (5 ml). The reaction was stirred for two hours at ambient temperature. The reaction was then diluted with dichloromethane and washed with 1N aqueous sodium hydroxide. The organics were dried over magnesium sulfate, filtered and concentrated to give the title compound (0.080 g, 87% yield).

Workup

  1. washwashed with 1N aqueous sodium hydroxide
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1ef955aef3024dfbb6fac916cf1ca0e7
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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