Ammonium Acetate → benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamate

HRID 2361394노트

반응식

HRID 2361394 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:15]([C:21]3[C:22]([CH3:38])=[C:23]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:24]=[CH:25][CH:26]=3)[CH:16]([N+:18]([O-])=O)[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1.C([O-])(=O)C.[NH4+]>CO.O1CCCC1.CCOC(C)=O.[Zn]>[NH2:18][CH:16]([CH3:17])[CH:15]([C:21]1[C:22]([CH3:38])=[C:23]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=[CH:25][CH:26]=1)[C:10]1[C:9]2[C:13](=[CH:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=2)[NH:12][CH:11]=1

참가 물질

7

반응물 2

HCID 517165Ammonium AcetateHCID 67994587benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate

생성물 1

HCID 67994898benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamate수율 92%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate (1.6194 g, 3.13 mmol), ammonium acetate (2.51 g, 46.9 mmol) and zinc (3.07 g, 46.9 mmol) in methanol (Ratio: 1.000, Volume: 57.9 ml) and tetrahydrofuran (Ratio: 1.000, Volume: 57.9 ml) was stirred under nitrogen. After 5 h, the reaction was diluted with EtOAc and filtered through a wad of CELITE®. The filtrate was concentrated in vacuo, and the residue was dissolved in EtOAc (75 mL) and saturated aqueous NaHCO3 (30 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2×75 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo to give benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamate (1.3975 g, 2.87 mmol, 92% yield, mixture of 2 isomers) as a colorless oil, LC/MS (M+H)=488.30, 488.30.

후처리

  1. filtrationfiltered through a wad of CELITE®
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (75 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×75 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ea51650a1a7d43d980df1f13d05ebe07
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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