(S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate → (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide

HRID 594822노트

반응식

HRID 594822 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C@H:13]([C:27]([NH:29][C:30]3[S:31][C:32]([F:35])=[CH:33][N:34]=3)=[O:28])[CH2:14][C@H:15]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1>Cl>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([C@@H:13]([CH2:14][C@H:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[C:27]([NH:29][C:30]3[S:31][C:32]([F:35])=[CH:33][N:34]=3)=[O:28])=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

참가 물질

3

반응물 1

HCID 73506951(S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate

생성물 1

HCID 118268346(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide수율 108.7%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

The (S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate (2.57 g, 4.91 mmol) obtained in Example 1 was dissolved in hydrochloric acid (4 M ethyl acetate solution, 10 mL), and the obtained mixture was then stirred for 10 minutes. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then dissolved in chloroform. The obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, was then dried over sodium sulfate, and was then concentrated in vacuo, so as to obtain (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide (2.26 g, quant) in the form of a white solid.

후처리

  1. concentrationThereafter, the reaction solution was concentrated in vacuo
  2. dissolutionthe obtained residue was then dissolved in chloroform
  3. washThe obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialwas then dried over sodium sulfate
  5. concentrationwas then concentrated in vacuo

출처 및 근거

ORD 기록
ord-756aa8ca2bc64aa089e280ef8856ba8d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242978B2

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