Methanol → N-[(4aR,7aR)-7a-(5-cyanothiophen-2-yl)-4,4a,5,6,7,7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 338138ノート

反応式

HRID 338138 の反応式
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][C@:14]2([C:29]2[S:30][C:31]([C:34]#[N:35])=[CH:32][CH:33]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C(#N)C.I[Si](C)(C)C>[C:34]([C:31]1[S:30][C:29]([C@:14]23[CH2:16][NH:17][CH2:18][C@H:13]2[CH2:12][S:11][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:15]3)=[CH:33][CH:32]=1)#[N:35]

参加物

5

反応物 2

HCID 887MethanolHCID 86762221Benzyl(4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

生成物 1

HCID 86762239N-[(4aR,7aR)-7a-(5-cyanothiophen-2-yl)-4,4a,5,6,7,7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide収率 118%

試薬・触媒・溶媒 2

HCID 85247Trimethylsilyl iodide触媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred clear and colorless solution of the benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (405 mg, 0.806 mmol) in acetonitrile (16 mL) under an atmosphere of nitrogen at room temperature is added iodotrimethylsilane (345 μL, 2.42 μmol). The resulting pale yellow solution is stirred at room temperature for 70 minutes. Methanol (391 μL, 9.67 mmol) is added and the pale yellow mixture is stirred for 5 minutes, and then concentrated under reduced pressure. The residue is partially purified by silica gel chromatography, eluting with a dichloromethane/methanol, gradient from 99:1 to 90:10, to give the title compound (349 mg, 118%) as a pale yellow solid (assume quantitative recovery and carry partially purified material into next step). MS/ES (m/z) 369.0 (M+H).

後処理

  1. stirringthe pale yellow mixture is stirred for 5 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partially purified by silica gel chromatography
  4. washeluting with a dichloromethane/methanol, gradient from 99:1 to 90:10

出典と根拠

ORDレコード
ord-26fbc79dbce74a2d821e19cc8ab765b0
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

反応ノート

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