Trifluoroacetic acid → HCID 57479136, compound

HRID 556491Notes

Reaction equation

HRID 556491 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:23]2([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=3)[C:31]3[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=3)[NH:25][C:24]2=[O:33])[CH2:15][C:16](=[O:22])[NH:17][CH:18]2[CH2:21][CH2:20][CH2:19]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:32][C:28]1[CH:27]=[C:26]2[C:31]([C:23]([N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:15][C:16]([NH:17][CH:18]3[CH2:19][CH2:20][CH2:21]3)=[O:22])([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=3)[C:24](=[O:33])[NH:25]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57479139HCID 57479139, compound

Product 1

HCID 57479136HCID 57479136, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 4-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-cyclobutylcarbamoylmethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester (700 mg, 1.17 mmol) was dissolved a mixture solution of CF3COOH and CH2Cl2. After stirred 0.5 h, the solution was concentrated and the organic layer was washed with NaOH aqueous solution. The organic layer was dried, concentrated to obtain crude product. The crude product was purified by chromatography to obtain 200 mg rac-2-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidin-4-yl-amino}-N-cyclobutyl-acetamide.

Workup

  1. concentrationthe solution was concentrated
  2. washthe organic layer was washed with NaOH aqueous solution
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto obtain crude product
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-d88dfe7be7da46ca8fc0e22566f5a0d9
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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