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

HRID 333352Notes

Reaction equation

HRID 333352 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:19]C(=O)OC(C)(C)C)[C:9]([N:11]([CH2:13][C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])=[O:10])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:19][C@@H:8]([CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:6][CH:5]=1)[C:9]([N:11]([CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68749501(S)-tert-butyl 3-(biphenyl-4-yl)-1-((furan-2-ylmethyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 68747189(S)-2-amino-3-(biphenyl-4-yl)-N-(furan-2-ylmethyl)-N-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(biphenyl-4-yl)-1-((furan-2-ylmethyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (614 mg) in CH2Cl2 (6 mL) was added TFA (3 mL). The mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure and azeotroped (three times) with toluene and dried under high vacuum. The crude (S)-2-amino-3-(biphenyl-4-yl)-N-(furan-2-ylmethyl)-N-methylpropanamide TFA salt (721 mg) was used for next step without further purification. HPLC retention time=1.37 minutes (condition B); MS (m+1)=335.0.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customazeotroped (three times) with toluene
  3. customdried under high vacuum
  4. customThe crude (S)-2-amino-3-(biphenyl-4-yl)-N-(furan-2-ylmethyl)-N-methylpropanamide TFA salt (721 mg) was used for next step without further purification

Sources & evidence

ORD record
ord-46c4b87866eb4610b79918884e20120d
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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