Trifluoroacetic acid → (2R)-3-Amino-N-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-propionamide

HRID 480185Notes

Reaction equation

HRID 480185 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10](=[O:38])[NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH2:25][CH:24]1[CH3:37])=[O:22])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C(=O)([O-])O.[Na+]>[NH2:7][CH2:8][CH2:9][C:10]([NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[CH2:25][C@H:24]1[CH3:37])=[O:22])=[O:38]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69911989[2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 12112108(2R)-3-Amino-N-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-propionamideYield 74.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [2-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (0.110 g, 0.2 mmol) in methylene chloride (3 mL) was added trifluoroacetic acid (0.50 mL). The reaction was stirred for 2 hours at ambient temperature then diluted with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with methylene chloride and the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (0.069 g)

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. dry with materialthe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-664a2f93ef454c8fa3de8907c22075a1
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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