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4-Acetylbenzoic Acid → [(2S,3S)-1-(4-acetyl-benzoyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

HRID 1486034
ノート
印刷プレビュー

反応式

HRID 1486034 の反応式
P(Cl)(Cl)(Cl)=O.[C:6]([O:10][C:11](=[O:26])[NH:12][C@H:13]1[C@H:19]([CH3:20])[NH:18][C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][C:14]1=[O:25])([CH3:9])([CH3:8])[CH3:7].[C:27]([C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)(=[O:29])[CH3:28]>N1C=CC=CC=1.O>[C:6]([O:10][C:11](=[O:26])[NH:12][C@H:13]1[C@H:19]([CH3:20])[N:18]([C:34](=[O:35])[C:33]2[CH:32]=[CH:31][C:30]([C:27](=[O:29])[CH3:28])=[CH:38][CH:37]=2)[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][C:14]1=[O:25])([CH3:7])([CH3:8])[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 114704-Acetylbenzoic AcidHCID 24813Phosphorus oxychlorideHCID 90082343tert-butyl(2S,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

生成物 1

HCID 90082505[(2S,3S)-1-(4-acetyl-benzoyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester収率 66.8%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 1049Pyridine溶媒

実験手順

Phosphoryl chloride (0.16 ml, 1.72 mmol) was added to a solution of ((2S,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (0.5 g, 1.72 mmol) and 4-acetyl-benzoic acid (0.25 g, 1.54 mmol) in pyridine (15 ml) at 0° C., stirring continued for 2 h. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (2×60 mL). The organic layers were combined, washed with 10% aqueous citric acid (1×15 mL), water (1×15 mL) and a saturated aqueous solution of sodium hydrogen carbonate (1×15 mL) and brine. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel gradient eluted with 10 to 60% v/v ethyl acetate hexanes to give [(2S,3S)-1-(4-acetyl-benzoyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester (0.45 g, 60%).

後処理

  1. extractionextracted with ethyl acetate (2×60 mL)
  2. washwashed with 10% aqueous citric acid (1×15 mL), water (1×15 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography over silica gel gradient
  8. washeluted with 10 to 60% v/v ethyl acetate hexanes

出典と根拠

ORDレコード
ord-87e5852b7d3d41c9aea67930d328d964
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422331B2

反応ノート

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