Dimethylamine → Benzyl [2-(dimethylcarbamoyl)ethyl]carbamate

HRID 1951171

反応式

HRID 1951171 の反応式
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2][CH2:3][C:4](O)=[O:5].C[CH2:18][N:19]=[C:20]=NCCCN(C)C.Cl.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.CNC>O1CCOCC1>[CH2:10]([O:9][C:7](=[O:8])[NH:1][CH2:2][CH2:3][C:4](=[O:5])[N:19]([CH3:20])[CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 5

HCID 674DimethylamineHCID 8471TriethylamineHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 19971000Benzyl [2-(dimethylcarbamoyl)ethyl]carbamate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

To a stirred, cooled (0° C.) solution of Z-Beta-Ala-OH (1.784 g, 8.0 mmol) in dioxane (20 ml) is added EDCI.HCl (2.145 g, 11.2 mmol), hydroxybenzotriazole (1.08 g, 8.0 mmol) and triethylamine (1.56 ml, 11.2 mmol). After stirring at 0° C. for 30 minutes, dimethylamine (0.397 g, 8.8 mmol) is added and stirring continued for a further hour. The reaction mixture was allowed to warm to room temperature and the solvent is removed in vacuo. Initial purification of the crude residue is carried out by flash chromatography of silica eluting with ethyl acetate. The combined organic factions are washed with water (3×20 ml), brine (1×50 ml) and dried over MgSO4. The solvent is removed in vacuo to yield the titled compound as a pale yellow solid.

後処理

  1. stirringstirring
  2. waitcontinued for a further hour
  3. temperatureto warm to room temperature
  4. customthe solvent is removed in vacuo
  5. customInitial purification of the crude residue
  6. washThe combined organic factions are washed with water (3×20 ml), brine (1×50 ml)
  7. dry with materialdried over MgSO4
  8. customThe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-4e132a516f2d4c90b2339b822fb1e7d8
出典データセット
uspto-grants-2013_03
特許番号
US08404684B2

関連ノート

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