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

HRID 2361272노트

반응식

HRID 2361272 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: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

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 67994685Benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

생성물 1

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

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3515c6bef63c4f1fa893ea62ecdfe660
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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