{(S)-1-[4-Fluoro-2-(6-fluoropyridin-3-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester → (S)-2-Amino-N-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenyl]propionamide

HRID 242992Notes

Reaction equation

HRID 242992 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:21]=[N:22][C:23]([F:26])=[CH:24][CH:25]=1)[CH3:9])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C@@H:8]([CH3:9])[C:10]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:21]=[N:22][C:23]([F:26])=[CH:24][CH:25]=1)=[O:27]

Participants

4

Reactant 1

HCID 68157060{(S)-1-[4-Fluoro-2-(6-fluoropyridin-3-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 68157286(S)-2-Amino-N-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenyl]propionamideYield 94.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of {(S)-1-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (276 mg, 0.70 mmol) in DCM (1 mL) and TFA (1 mL) was stirred at RT for 3 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge then washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford the title compound as a yellow oil (193 mg, 94%). LCMS (Method C): RT 0.29 and 1.93 min [M+H]+ 293.2.

Workup

  1. washthen washed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-721367ae485547a9a6c07da07d63a4da
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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