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

HRID 2361394ノート

反応式

HRID 2361394 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ea51650a1a7d43d980df1f13d05ebe07
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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