Cesium carbonate → Benzyl 4-(2-hydroxyethylthio)-2-methylbutan-2-ylcarbamate

HRID 1770681ノート

反応式

HRID 1770681 の反応式
[SH:1][CH2:2][CH2:3][C:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH3:5].I[CH:19]([OH:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:21][CH2:19][CH2:20][S:1][CH2:2][CH2:3][C:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 178599451-IodoethanolHCID 86665509HCID 86665509、化合物

生成物 1

HCID 67508326Benzyl 4-(2-hydroxyethylthio)-2-methylbutan-2-ylcarbamate収率 27.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (3.30 g, 12.2 mmol) in N,N-dimethylformamide (50 ml) was added iodoethanol (1.4 ml, 18.0 mmol) and cesium carbonate (390 mg, 1.20 mmol). The solution was heated to 85° C. for 16 hours, cooled to room temperature, and concentrated in vacuo. The residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (1.01 g, 3.40 mmol, 26%). 1H NMR (400 MHz, CDCl3) δ 1.31 (s, 6H), 2.0-2.1 (m, 2H), 2.47-2.51 (m, 2H), 2.72 (m, 2H), 3.70 (m, 2H), 4.7 (s, 1H), 5.06 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 298 [M+H]+, 320 [M+Na]+.

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-e2e1c5bf7992449bbc1e50c56646dcb6
出典データセット
uspto-grants-2016_02
特許番号
US09248117B2

反応ノート

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