(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 594822ノート

反応式

HRID 594822 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-756aa8ca2bc64aa089e280ef8856ba8d
出典データセット
uspto-grants-2016_01
特許番号
US09242978B2

反応ノート

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