Trifluoroacetic acid → HCID 46866394, compound

HRID 2367058Notes

Reaction equation

HRID 2367058 reaction equation
[CH3:1][C:2]1([CH3:45])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:43])[C@@H:18]([NH:27][C:28]([C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]3)=[O:29])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)[C:3]1=[O:44].FC(F)(F)C(O)=O>>[CH3:1][C:2]1([CH3:45])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:43])[C@@H:18]([NH:27][C:28]([C@@H:30]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]3)=[O:29])[CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:15][CH2:16]2)[C:3]1=[O:44]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66616116HCID 66616116, compound

Product 1

HCID 46866394HCID 46866394, compoundYield 83.5%

Procedure

A mixture of (R)-tert-butyl 3-((S)-1-(4-(3,3-dimethyl-2-oxoindolin-1-yl)piperidin-1-yl)-1-oxo-4-phenylbutan-2-ylcarbamoyl)piperidine-1-carboxylate (615 mg, 0.997 mmol, EXAMPLE 1, Alternative Method, Step 1) and trifluoroacetic acid (2 mL) was stirred for 20 min and concentrated. The residue was diluted with dichloromethane and basified by saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product was purified by amine gel column chromatography (dichloromethane/methanol, gradient) to give the title compound (430 mg, 83%) as an amorphous solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by amine gel column chromatography (dichloromethane/methanol, gradient)

Sources & evidence

ORD record
ord-391ae45e6af84aecb0e731051e06c611
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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