Trifluoroacetic acid → HCID 86629122, compound

HRID 1171156Notes

Reaction equation

HRID 1171156 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)=[CH:22][C:21]=3[Cl:34])[C:15]2=[O:35])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>C(Cl)Cl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[Cl:34][C:21]1[CH:22]=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[CH:24]=[C:25]([Cl:26])[C:20]=1[CH2:19][C@@H:16]1[CH2:17][CH2:18][N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15]1=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57647089HCID 57647089, compound

Product 1

HCID 86629122HCID 86629122, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 4-[(R)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Preparation 17) (0.85 g, 0.18 mmol) in CH2Cl2 (10 mL) with Trifluoroacetic acid (2 mL). Stir the reaction 1 hr at room temperature. Concentrate the reaction in vacuo. Purify the crude on a SCX column using 2M NH4 in MeOH to elute the pure product. Remove the solvent to afford 0.59 g (85%) of product. MS (m/e): 421 (M+1).

Workup

  1. customthe reaction 1 hr at room temperature
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. customPurify the crude on a SCX column
  5. washto elute the pure product
  6. customRemove the solvent

Sources & evidence

ORD record
ord-4174e1795f3746c9a6f9fca62f706d2f
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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