Trifluoroacetic acid → (S)-2-Amino-3-(6-bromopyridin-3-yl)propanamide

HRID 600303Notes

Reaction equation

HRID 600303 reaction equation
[NH2:1][C:2](=[O:20])[C@@H:3]([NH:12]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:6]=[N:7][C:8]([Br:11])=[CH:9][CH:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:12][C@@H:3]([CH2:4][C:5]1[CH:6]=[N:7][C:8]([Br:11])=[CH:9][CH:10]=1)[C:2]([NH2:1])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57999677(S)-tert-Butyl 1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 57999679(S)-2-Amino-3-(6-bromopyridin-3-yl)propanamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamate (1.5 g) was dissolved in DCM (20 mL) and to the solution was added TFA (10 mL). The reaction mixture was stirred for 0.5 h then concentrated in vacuo. Crude material was dissolved in methanol and loaded onto an SCX cartridge. Non-basic impurities were washed off with methanol, then product was eluted with 10% ammonia in methanol to give the sub-title compound (1.0 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionCrude material was dissolved in methanol
  3. washNon-basic impurities were washed off with methanol
  4. washproduct was eluted with 10% ammonia in methanol

Sources & evidence

ORD record
ord-3ae7fb5fba294b2d91e067cb7922e988
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

Loading…