Triethylamine → 3-(Ethoxycarbonylpropyl]urea

HRID 974013노트

반응식

HRID 974013 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 543213273-(Ethoxycarbonylpropyl]urea수율 180.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e65a6c9213a4d2bab96e07fbf3570e3
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066658

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