Ammonium Chloride → Tert-butyl 4-allyl-3-[(2-aminophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate

HRID 590733노트

반응식

HRID 590733 반응식
[CH2:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]1([C:23](=[O:34])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-])=O)[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:2]=[CH2:3].[Cl-].[NH4+]>CO.C(OCC)(=O)C.[Zn]>[CH2:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]1([C:23](=[O:34])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31])[NH:16][C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])[CH:2]=[CH2:3]

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 86665787Tert-butyl 4-allyl-3-[(2-nitrophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate

생성물 1

HCID 86665788Tert-butyl 4-allyl-3-[(2-aminophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate수율 99.1%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of tert-butyl 4-allyl-3-[(2-nitrophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate (0.816 g, 1.68 mmol) in methanol (30 mL) was treated with ammonium chloride (0.897 g, 16.8 mmol) and zinc (2.19 g, 33.5 mmol). After stirring at room temperature for 40 min, the mixture was diluted with ethyl acetate (30 mL) and filtered through a pad of Celite. The pad was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was re-diluted with ethyl acetate (25 mL) and water (20 mL), and the layers were separated. The organic phase was washed with water (10 mL) and saturated aqueous sodium chloride (10 mL), dried over Na2SO4 and concentrated and dried under high vacuum for ˜2 h to give the tert-butyl 4-allyl-3-[(2-aminophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate intermediate (760 mg, 3:2 mixture of diastereomers) as a off-white foam that was used without further purification.

후처리

  1. filtrationfiltered through a pad of Celite
  2. washThe pad was washed with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was re-diluted with ethyl acetate (25 mL) and water (20 mL)
  5. customthe layers were separated
  6. washThe organic phase was washed with water (10 mL) and saturated aqueous sodium chloride (10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customdried under high vacuum for ˜2 h

출처 및 근거

ORD 기록
ord-a1cfbf392e6b49e382efb372b01420d5
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233985B2

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