Trifluoroacetic acid → N1-Isobutyl-L-alaninamide

HRID 1062903Notes

Reaction equation

HRID 1062903 reaction equation
C(OC([NH:8][C@H:9]([C:11]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:14]([NH:13][C:11](=[O:12])[C@H:9]([CH3:10])[NH2:8])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 28168390N2-(tert-butoxycarbonyl)-N1-isobutyl-L-alaninamide

Product 1

HCID 13750006N1-Isobutyl-L-alaninamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N2-(tert-Butoxycarbonyl)-N1-isobutyl-L-alaninamide (300 mg, 1.23 mmol) is stirred with 2 mL of TFA in 4 mL of dichloromethane for 1 h. The mixture is concentrated and neutralized with 2 mL of 1 N NaHCO3 and 2 mL of 1 N Na2CO3, and extracted into 50 mL of ethyl ether containing 2 mL of methanol. The organic phase was washed with brine and dried with Na2SO4. Concentration afforded the title compound as a colorless film (90 mg, 0.62 mmol, 51%). 1H NMR (CD3OD) δ 4.9 (s, 3H, includes water), 3.52 (q, J=7 Hz, 1H), 3.07-2.96 (m, 2H), 1.78 (m, 1H), 1.31 (d, J=7 Hz, 3H), 0.90 (m, 6H)

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted into 50 mL of ethyl ether containing 2 mL of methanol
  3. washThe organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-01f218fcf7df4e7b9679490e7d31c7a6
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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