Trifluoroacetic acid → HCID 74928536, compound

HRID 504543Notes

Reaction equation

HRID 504543 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[CH:28]2[CH2:33][C:32](=[O:34])[NH:31][CH:30]([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[CH3:42])[C:29]32[C:50]2[C:45](=[CH:46][C:47]([Cl:51])=[CH:48][CH:49]=2)[NH:44][C:43]3=[O:52])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[Cl:51][C:47]1[CH:46]=[C:45]2[NH:44][C:43](=[O:52])[C:29]3([CH:28]([C:22]4[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=4[N:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)[CH2:33][C:32](=[O:34])[NH:31][CH:30]3[C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[CH3:42])[C:50]2=[CH:49][CH:48]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 74928508HCID 74928508, compound

Product 1

HCID 74928536HCID 74928536, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, trifluoroacetic acid (2 mL) was added into a solution of racemic (2′S,3S,4′R)-4′-[2-(4-tert-butoxycarbonyl-piperazin-1-yl)-5-chloro-phenyl]-6-chloro-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (280 mg, 0.43 mmol) in DCM (10 mL). After stirred for 2 h, the mixture was concentrated. The residue was dissolved in EtOAc, washed with 1 N NaOH and water, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow solid (230 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1 N NaOH and water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-18a7f5593ebd4f1d81862db0576e5a39
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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