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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
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HRID 1486034 반응식
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]
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참가 물질

6

반응물 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

생성물 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 ester수율 66.8%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-87e5852b7d3d41c9aea67930d328d964
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09422331B2

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