Ammonium Chloride → (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate

HRID 632779ノート

反応式

HRID 632779 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.[C:8]([O:12][C:13](=[O:27])[C@@H:14]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][C:16](O)=[O:17])([CH3:11])([CH3:10])[CH3:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+]>CN(C=O)C>[C:23]([O:22][C:20]([NH:19][C@@H:14]([CH2:15][C:16]([NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:17])[C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:27])=[O:21])([CH3:26])([CH3:25])[CH3:24]

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 7010517(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 118061281(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate収率 91.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-methyl-1H-pyrazol-3-amine (0.336 g) and (3S)-4-tert-butoxy-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (1.0 g) in DMF (17.28 mL) were added HATU (1.577 g) and diisopropylethylamine (0.905 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.17 g).

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-3bcbeb297eeb40a7a1a72265e5c884a7
出典データセット
uspto-grants-2016_04
特許番号
US09321757B2

反応ノート

読み込み中…