Triethylamine → 3-(Ethoxycarbonylpropyl]urea

HRID 974013ノート

反応式

HRID 974013 の反応式
C([N:11]=[C:12]=[O:13])CCCCCCCCC.Cl.C(O[NH:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])C1C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:30]([O:29][C:27]([CH2:26][CH2:25][CH2:24][NH:23][C:12](=[O:13])[NH2:11])=[O:28])[CH3:31]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 4420451Decyl isocyanateHCID 19987251Ethyl 4-(benzyloxyamino)butyrate hydrochloride

生成物 1

HCID 543213273-(Ethoxycarbonylpropyl]urea収率 180.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

Using the method of Example 2 above, but using ethyl 4-bromobutyrate, t-butyl N-[3-(ethoxycarbonyl)propyl]-N-benzyloxy carbamate was obtained as a colorless oil. This carbamate (6.17 g, 18.8 mmol) was dissolved in 3.3M HCl in ethyl acetate (50 ml) at room temperature under nitrogen. After one hour, the turbid solution was evaporated, and the residue was triturated with hexane. Filtration gave ethyl 4-(benzyloxyamino)butyrate hydrochloride as a white solid (4.59 g, 93% yield). To a solution of decyl isocyanate (0.92 g) in toluene (50 ml) was added this hydrochloride (1.40 g) in DMF (5 ml). Triethylamine (0.75 ml) was added, and the solution was stirred for one hour. The mixture was washed with 10% aqueous citric acid, and the organic solution was dried (MgSO4), filtered and evaporated. Purification by chromatography on silica gave N'-decyl-N-benzyloxy-N-[3-(ethoxycarbonylpropyl]urea as a colorless oil (1.58 g, 58% yield).

後処理

  1. washThe mixture was washed with 10% aqueous citric acid
  2. dry with materialthe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography on silica

出典と根拠

ORDレコード
ord-3e65a6c9213a4d2bab96e07fbf3570e3
出典データセット
uspto-grants-1991_11
特許番号
US05066658

反応ノート

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