HCID 66616105, compound → HCID 46912482, compound

HRID 2367065Notes

Reaction equation

HRID 2367065 reaction equation
[CH3:1][C:2]1([CH3:46])[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:44])[C@@H:18]([NH:27][C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([N:35](C)[C:36](=O)OC(C)(C)C)[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:45]>ClCCl.FC(F)(F)C(O)=O>[CH3:1][C:2]1([CH3:46])[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:44])[C@@H:18]([NH:27][C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([NH:35][CH3:36])[CH2:31]3)=[O:29])[CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:13][CH2:12]2)[C:3]1=[O:45]

Participants

3

Reactant 1

HCID 66616105HCID 66616105, compound

Product 1

HCID 46912482HCID 46912482, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of tert-butyl (S)-1-((S)-1-(4-(3,3-dimethyl-2-oxoindolin-1-yl)piperidin-1-yl)-1-oxo-4-phenylbutan-2-ylcarbamoyl)pyrrolidin-3-yl(methyl)carbamate (267 mg, 0.42 mmol, EXAMPLE 47: Alternative Method, Step 1) in dichloromethane-trifluoroacetic acid (1:1, 6 mL) was stirred at room temperature for 1 h. The mixture was concentrated, diluted with dichloromethane, and washed with saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residual oil was purified by preparative HPLC (32-96% methanol in 0.01% ammonia aqueous solution) and by amino gel column chromatography to give the title compound (209 mg, 93%) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with dichloromethane
  3. washwashed with saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil was purified by preparative HPLC (32-96% methanol in 0.01% ammonia aqueous solution) and by amino gel column chromatography

Sources & evidence

ORD record
ord-6a59d5f21c614bf89bd5bd0e6e00cb1b
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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