Trifluoroacetic acid → (S)-2-amino-3-(biphenyl-4-yl)-N-methylpropanamide

HRID 333349Notes

Reaction equation

HRID 333349 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:13]C(=O)OC(C)(C)C)[C:9]([NH:11][CH3:12])=[O:10])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:13][C@@H:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:2][CH:3]=1)[C:9]([NH:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10498346(S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 10708666(S)-2-amino-3-(biphenyl-4-yl)-N-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate (111 mg, 0.31 mmol) in DCM (4 mL) was added TFA (2 mL). The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and azeotroped (three times) with toluene and dried under high vacuum. The obtained (S)-2-amino-3-(biphenyl-4-yl)-N,N-methylpropanamide TFA salt (80 mg) was used for next step without further purification. HPLC retention time=1.21 minutes (condition B); MS (m+1)=255.0; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.48 (d, J=1.8 Hz, 3H) 2.90-3.24 (m, 2H) 4.04-4.48 (m, 1H) 7.10 (d, J=8.3 Hz, 2H) 7.20 (d, J=7.3 Hz, 1H) 7.26 (t, J=7.5 Hz, 2H) 7.37 (d, J=7.6 Hz, 4H) 8.16 (br. s., 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped (three times) with toluene
  3. customdried under high vacuum
  4. customThe obtained (S)-2-amino-3-(biphenyl-4-yl)-N,N-methylpropanamide TFA salt (80 mg) was used for next step without further purification

Sources & evidence

ORD record
ord-b5fda54f34b245e48bf9553417b750b2
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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