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

HRID 61389ノート

反応式

HRID 61389 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-298fbd0c3adb4c1ba391ad542a1243ce
出典データセット
uspto-grants-2016_09
特許番号
US09440995B2

反応ノート

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