Trifluoroacetic acid → (S)-2-Amino-3-(4'-cyanobiphenyl-4-yl)propanamide

HRID 216910Notes

Reaction equation

HRID 216910 reaction equation
[NH2:1][C:2](=[O:27])[C@@H:3]([NH:19]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:19][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[C:2]([NH2:1])=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59568594(S)-tert-Butyl 1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 59568596(S)-2-Amino-3-(4'-cyanobiphenyl-4-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-amino-3-(4′-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamate (Example 3, step (ii), 3.13 g) was dissolved in dichloromethane (30 mL) and TFA (1.32 mL) was added. The dichloromethane was distilled off on a rotary evaporator at atmospheric pressure to leave ˜5 mL of solvent. The reaction was monitored by HPLC/MS and when complete was partitioned between water and dichloromethane. The organic layer was separated and the aqueous layer further extracted with dichloromethane. The combined organic extracts were dried (magnesium sulfate) and evaporated. The resulting solid was purified by chromatography on silica eluting with ethyl acetate then ethyl acetate containing 10% methanol to afford the sub-titled compound (1.95 g).

Workup

  1. distillationThe dichloromethane was distilled off on a rotary evaporator at atmospheric pressure

Sources & evidence

ORD record
ord-2ade0a11f9484468a056a268e37f3575
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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