Trifluoroacetic acid → HCID 53357367, 화합물

HRID 1807277노트

반응식

HRID 1807277 반응식
[Cl:1][C:2]1[C:3]([F:47])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:46]=[CH:45][C:34]([CH2:35][CH2:36][NH:37]C(=O)OC(C)(C)C)=[CH:33][CH:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:37][CH2:36][CH2:35][C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:28]([C@H:9]2[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:47])[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10]2)=[O:29])=[CH:46][CH:45]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 53357366HCID 53357366, 화합물

생성물 1

HCID 53357367HCID 53357367, 화합물수율 61.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)phenethylcarbamate (77.3 mg, 0.113 mmol) in dichloromethane (3 ml) was treated with trifluoroacetic acid (2.23 g, 19.6 mmol) and stirred under argon. After 1.5 hrs, the reaction mixture was concentrated and the residue diluted with ethyl acetate, washed with saturated sodium carbonate, water and brine to give chiral (2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [4-(2-amino-ethyl)-phenyl]-amide (40.6 mg, 54.2%) as a white lyophilized solid.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with saturated sodium carbonate, water and brine

출처 및 근거

ORD 기록
ord-848b20bffe80402e8495590c24f9c290
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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