4-Methylmorpholine → ({[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-methyl}-tert-butoxycarbonyl-amino)-acetic acid

HRID 79712

反応式

HRID 79712 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[O:11][C:10](=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)=[O:20].CN1CCOCC1>CN(C)C=O>[Br:27][C:24]1[CH:23]=[CH:22][C:21]([C:19](=[O:20])[CH2:18][NH:17][C:12]([CH2:13][N:8]([CH2:9][C:10]([OH:11])=[O:15])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:14])=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 11830836Tert-butyl 2,6-dioxomorpholine-4-carboxylate

生成物 1

HCID 59611182({[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-methyl}-tert-butoxycarbonyl-amino)-acetic acid収率 80.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2,6-Dioxo-morpholine-4-carboxylic acid tert-butyl ester (2.5 g, 11.6 mmol) was added to a solution of 2-amino-1-(4-bromo-phenyl)-ethanone hydrochloride (3.05 g, 12.2 mmol) and 4-methylmorpholine (1.92 mL, 17.4 mmol) in dimethylformamide (15 mL). After 30 min the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with water (50 mL), aqueous hydrogen chloride (0.5 N, 2×50 mL), and saturated sodium bicarbonate (2×50 mL). The basic extracts were neutralized and extracted with ethyl acetate (2×75 mL). The combined organic phases from the second extraction were dried over sodium sulfate, and filtered. The solvent was removed under reduced pressure to provide ({[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-methyl}-tert-butoxycarbonyl-amino)-acetic acid (4 g, 9.3 mmol, 80%). C17H21BrN2O6 calculated 428.0 observed [M+1]+ 431.1; rt=2.36 min.

後処理

  1. customAfter 30 min the solvent was removed under reduced pressure
  2. washwashed with water (50 mL), aqueous hydrogen chloride (0.5 N, 2×50 mL), and saturated sodium bicarbonate (2×50 mL)
  3. extractionextracted with ethyl acetate (2×75 mL)
  4. extractionThe combined organic phases from the second extraction
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-9d840e0cf03446569270480f17560e27
出典データセット
uspto-grants-2014_09
特許番号
US08841278B2

関連ノート

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