Triethylamine → Benzyl tert-butyl malonate

HRID 1616997ノート

反応式

HRID 1616997 の反応式
[C:1]([O:5][C:6](=[O:12])NCC(=O)N)([CH3:4])([CH3:3])[CH3:2].[CH2:13](N(CC)CC)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C([O-])([O-])=O.[Na+].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:24]([O:23][C:21](=[O:22])[CH2:13][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:12])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

生成物 1

HCID 2736712Benzyl tert-butyl malonate収率 95.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Carbamoylmethyl-carbamic acid tert-butyl ester (8a; 0.84 g, 4.8 mmol) was dissolved in dichloromethane (10 mL), and added with triethylamine (1.0 mL, 7.2 mmol) and benzyl chloroformate (0.85 g, 0.75 mL, 5.0 mmol) at 0° C. After stirring for 5 min, 4-dimethylaminopyridine (DMAP; 0.32 g, 2.6 mmol) was added slowly with continuous stirring at 0° C. for 1 h. After the reaction is completed, dichloromethane (10 mL) and saturated Na2CO3 solution (10 mL) were added. The organic phase was washed by H2O (10 mL), 1N HCl (20 mL), H2O (20 mL) and saturated NaCl solution (20 mL) separately, and dried over MgSO4 and concentrated under reduced pressure to remove dichloromethane to obtain white solid product 12 (1.15 g; 95%). 1H-NMR (200 MHz) (CDCl3) δ: 7.30˜7.38 (m, 5H, ArH), 5.17 (s, 2H, CO2CH2Ph), 5.02 (br, s, 1H, NHBOC), 3.94 (d, 2H, Gly-H), 1.43 [s, 9H, CO2C(CH3)3]

後処理

  1. stirringwith continuous stirring at 0° C. for 1 h
  2. washThe organic phase was washed by H2O (10 mL), 1N HCl (20 mL), H2O (20 mL) and saturated NaCl solution (20 mL) separately
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto remove dichloromethane

出典と根拠

ORDレコード
ord-9edbb5fd57f94745ba1d1c2d4ac135e7
出典データセット
uspto-grants-2014_07
特許番号
US08765934B2

反応ノート

読み込み中…