Sodium methanethiolate → benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate

HRID 533220ノート

反応式

HRID 533220 の反応式
CS(O[CH2:6][C@H:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]1)(=O)=O.[CH3:26][S-:27].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:14][C:10]1([CH3:13])[O:9][C@H:8]([C@@H:7]([NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:6][S:27][CH3:26])[CH2:12][O:11]1

参加物

5

反応物 2

HCID 4378561Sodium methanethiolateHCID 59131551HCID 59131551、化合物

生成物 1

HCID 58287015benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate収率 89.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of the product from Example 27.2 (2.58 g, 6.91 mmol) in dimethylformamide (10 ml) was added sodium thiomethoxide (0.630 g, 8.98 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with water (4×), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (ethyl acetate-petrol, 1:4) giving a colourless oil (2.007 g, 89%). 1H NMR (CDCl3) δ 7.35 (m, 5H), 5.12 (ABq, 2H), 5.07 (br. s, 1H), 4.47 (bit, J=7.2 Hz, 1H), 4.05 (t, J=7.2 Hz, 1H), 3.83 (brq, J=7.2 Hz, 1H), 3.70 (dd, J=8.3, 6.8 Hz, 1H), 2.69 (d, J=7.6 Hz, 2H), 2.15 (s, 3H), 1.42 (s, 3H), 1.34 (s, 3H).

後処理

  1. washwashed with water (4×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (ethyl acetate-petrol, 1:4)

出典と根拠

ORDレコード
ord-6862a19efb7f42d19e25a814c8957cc5
出典データセット
uspto-grants-2014_10
特許番号
US08853224B2

反応ノート

読み込み中…