Triethylamine → Tert-butyl [3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]carbamate

HRID 1715251

反応式

HRID 1715251 の反応式
[CH3:1][C:2]1([CH3:7])[CH2:6][O:5][CH2:4][NH:3]1.[C:8]([NH:15][CH2:16][CH2:17][C:18](O)=[O:19])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:1][C:2]1([CH3:7])[CH2:6][O:5][CH2:4][N:3]1[C:18](=[O:19])[CH2:17][CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 620104,4-Dimethyl oxazolidineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

生成物 1

HCID 86621990Tert-butyl [3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]carbamate収率 139.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21867204Cyclohexane ethylacetate溶媒

実験手順

To a mixture of 4,4-dimethyloxazolidine (287 μl; 2 mmol; 1 eq) and boc-beta-alanine (416.3 mg; 2.2 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (832 μl; 6 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1533 mg; 6 mmol; 3 eq). The mixture is stirred for 2 days at RT. The reaction is followed by TLC cyclohexane/EtOAc 1:1). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated to give 760 mg of an orange oil, which is purified by flash chromatography (cyclohexane/EtOAc gradient, from 9/1 to 1/1 over 30 min). The title product is isolated as a white-off solid (420.5 mg; 77%).

後処理

  1. washThe reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-aebc291accbd4055ad19e939995446b1
出典データセット
uspto-grants-2010_09
特許番号
US07799814B2

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