Triethylamine → [3-Benzyloxy-1(R)-cyanomethyl-propyl]-carbamic acid tert-butyl ester

HRID 564356ノート

反応式

HRID 564356 の反応式
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]([CH2:19]O)[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(C)(=O)=O.[CH2:27]([N:29](CC)CC)C.[C-]#N.[NH4+].[NH4+].[NH4+].[NH4+].[C-]#N.[C-]#N.[C-]#N>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([CH2:19][C:27]#[N:29])[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21087273tert-Butyl 3-(benzyloxy)-1-(hydroxymethyl)propylcarbamateHCID 86614618Tetraammonium cyanide

生成物 1

HCID 67006795[3-Benzyloxy-1(R)-cyanomethyl-propyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(3-Benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester (7.4 g, 25 mmole) was dissolved in 100 ml DCM. Mesyl chloride (4.3 g, 37.5 mmole) and triethylamine (5.0 g, 50 mmole) were added. The reaction was stirred at room temperature for 20 minutes. 100 ml DCM and 100 ml water were added. The organic layer washed with brine (100 ml), dried over sodium sulfate and concentrated. The residue was dissolved in 200 ml toluene. Tetraammonium cyanide (10 g, 37.5 mmole) was added and the reaction was stirred at room temperature overnight. The organic layer washed with water (2×100 ml), brine (100 ml), dried over sodium sulfate and concentrated. The residue was purified by column (EtOAc/hexane from 100/0 to 30/70 in 45 minutes). Yield, 6.4 g, 84%. 1H NMR (CDCl3 400 MHz δ 7.29-7.38 (m, 5H), 5.20 (d, J=5.9 Hz, 1H), 4.50 (m, 2H), 3.91 (m, 1H), 3.54-3.66 (m, 2H), 2.60-2.77 (m, 2H), 1.89-1.99 (m, 2H), 1.44 (s, 9H).

後処理

  1. washThe organic layer washed with brine (100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 200 ml toluene
  5. stirringthe reaction was stirred at room temperature overnight
  6. washThe organic layer washed with water (2×100 ml), brine (100 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column (EtOAc/hexane from 100/0 to 30/70 in 45 minutes)
  10. customYield

出典と根拠

ORDレコード
ord-6f847be5cb2a4ed29c140f77d569ca54
出典データセット
uspto-grants-2011_11
特許番号
US08067621B2

反応ノート

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