Ammonium Chloride → Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

HRID 2361272ノート

反応式

HRID 2361272 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:20]3[C:21]([CH3:37])=[C:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=[CH:24][CH:25]=3)[CH2:16][N+:17]([O-])=O)=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1.CO.C(OCC)(=O)C.[Zn]>[NH2:17][CH2:16][CH:15]([C:20]1[C:21]([CH3:37])=[C:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=[CH:24][CH:25]=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 25517Ammonium ChlorideHCID 67994685Benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

生成物 1

HCID 67994818Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate収率 100%

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 mixture of benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate (1.75 g, 3.48 mmol), ammonium chloride (2.79 g, 52.1 mmol), and zinc dust (3.41 g, 52.1 mmol) in tetrahydrofuran (35 mL) and methanol (35 mL) was stirred at room temperature for 4.5 hr. The mixture was diluted with ethyl acetate (40 mL) and filtered through CELITE®. The filtrate was concentrated under vacuum, and the residue was diluted with water (40 mL), basified with saturated NaHCO3 solution, and extracted with ethyl acetate (4×40 mL). The combined extract was washed with brine (40 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (1.65 g, 3.48 mmol, 100% yield) as beige solid.

後処理

  1. filtrationfiltered through CELITE®
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionthe residue was diluted with water (40 mL)
  4. extractionextracted with ethyl acetate (4×40 mL)
  5. extractionThe combined extract
  6. washwas washed with brine (40 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customRemoval of solvent under vacuum

出典と根拠

ORDレコード
ord-3515c6bef63c4f1fa893ea62ecdfe660
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

読み込み中…