Water → (S)-3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxamide

HRID 594825ノート

反応式

HRID 594825 の反応式
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C@@H:13]([CH2:23][C@H:24]3[CH2:28][CH2:27][NH:26][CH2:25]3)[C:14]([NH:16][C:17]3[S:18][C:19]([F:22])=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C[Si]([N:33]=[C:34]=[O:35])(C)C.O>ClCCl>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([C@H:13]([C:14]([NH:16][C:17]3[S:18][C:19]([F:22])=[CH:20][N:21]=3)=[O:15])[CH2:23][C@H:24]3[CH2:28][CH2:27][N:26]([C:34]([NH2:33])=[O:35])[CH2:25]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 118268346(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide

生成物 1

HCID 73506954(S)-3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxamide収率 99.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide (20.0 mg, 47.2 μmol) obtained in Step 1 of Example 2 was dissolved in dichloromethane (1 mL), and trimethylsilyl isocyanate (25.0 μL, 188 μmol) was then added to the obtained solution. The obtained mixture was stirred for hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo. The obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→20%) to obtain the captioned compound (22.0 mg, 99%) in the form of a white solid.

後処理

  1. extractionthe mixed solution was then extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→20%)

出典と根拠

ORDレコード
ord-65f3e94e2c5743e58b29ae7d74abdb3b
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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