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

HRID 216910ノート

反応式

HRID 216910 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-2ade0a11f9484468a056a268e37f3575
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

読み込み中…