Trifluoroacetic acid → HCID 86664838, compound

HRID 1628305Notes

Reaction equation

HRID 1628305 reaction equation
[O:1]=[C:2]([N:19]1[C:27]2[C:22](=[C:23]([C:34]3[O:35][C:36](=[O: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.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[OH:46][C:40]([C:42]([F:45])([F:44])[F:43])=[O:41].[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](=[O: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 67498238HCID 67498238, compound

Product 1

HCID 86664838HCID 86664838, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 ml flask containing (S)-tert-butyl 1-oxo-1-(4-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-6-(pyridin-4-yl)indolin-1-yl)-3-phenylpropan-2-ylcarbamate was added 20 ml of DCM and 10 ml of TFA. The reaction was stirred at room temperature for 6 hours at which time the solvent was removed with a stream of nitrogen to give (S)-5-(1-(2-amino-3-phenylpropanoyl)-6-(pyridin-4-yl)indolin-4-yl)-1,3,4-oxadiazol-2(3H)-one TFA salt 57.1.C (97 mg, 100% yield), which was used in the next step with no further purification.

Workup

  1. customwas removed with a stream of nitrogen

Sources & evidence

ORD record
ord-7e4062605b4a44188653640dabb3b1bf
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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