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

HRID 216910노트

반응식

HRID 216910 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

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

출처 및 근거

ORD 기록
ord-2ade0a11f9484468a056a268e37f3575
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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