Trifluoroacetic acid → HCID 86664839, compound

HRID 1628307Notes

Reaction equation

HRID 1628307 reaction equation
[O:1]=[C:2]([N:19]1[C:27]2[C:22](=[C:23]([C:34]3[O:35][C:36](=[S:39])[NH:37][N:38]=3)[CH:24]=[C:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:26]=2)[CH2:21][CH2:20]1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:2]([N:19]1[C:27]2[C:22](=[C:23]([C:34]3[O:35][C:36](=[S:39])[NH:37][N:38]=3)[CH:24]=[C:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:26]=2)[CH2:21][CH2:20]1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86664840HCID 86664840, compound

Product 1

HCID 86664839HCID 86664839, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-tert-butyl 1-oxo-3-phenyl-1-(6-(pyridin-4-yl)-4-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)indolin-1-yl)propan-2-ylcarbamate 58.0 (80 mg) was added 3 mL dichloromethane and 1.5 mL trifluoroacetic acid. Stirring was continued for a few hours until deprotection was complete. Reaction was concentrated, basified with NaHCO3 and extracted with 30% isopropanol in chloroform six times to afford 41 mg (63%) 58.D.

Workup

  1. waitwas continued for a few hours until deprotection
  2. customReaction
  3. concentrationwas concentrated
  4. extractionextracted with 30% isopropanol in chloroform six times

Sources & evidence

ORD record
ord-6d5cdc757c714357b12a3ff184eeafd6
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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