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

HRID 216910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216910
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2ade0a11f9484468a056a268e37f3575
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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