Ethyl Acetate → HCID 54305290、化合物

HRID 502324ノート

反応式

HRID 502324 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C(OC(NC(CNC1C=CC=CC=1N)C(O)=O)=O)(C)(C)C.[C:54]([O:57][CH2:58]C)(=[O:56])[CH3:55]>CN(C)C=O>[CH3:58][O:57][C:54](=[O:56])[CH2:55][N:14]1[C:15](=[O:16])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]1=2

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22243668HCID 22243668、化合物HCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

生成物 1

HCID 54305290HCID 54305290、化合物収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3(S)-tert-Butoxycarbonylamino-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.54 g, 44.5 mmol) was added to a cooled (0° C.) solution of 2-tert-butoxycarbonylamino-3-(2-aminophenylamino)propionic acid (11.95 g, 40.5 mmol) in 100 ml of dimethylformamide and stirred for 18 hours. The reaction was poured into 700 ml of ethyl acetate and washed four times with 100 ml of water. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to give a brown solid that was purified by flash chromatography eluting with 3:7 ethyl acetate/hexane to give 8 g (71%) of the title compound: 1H NMR (CDCl3) δ7.78 (1H, s), 7.02-6.95 (1H, m), 6.88-6.82 (1H, m), 6.82-6.78 (1H, m), 6.75-6.70 (1H, m), 5.8-5.7 (1H, d), 4.55-4.45 (1H, m), 3.95 (1H, s), 3.9-3.82 (1H, m), 3.48-3.40 (1H, m), 1.45 (9H, s).

後処理

  1. washwashed four times with 100 ml of water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a brown solid that
  6. customwas purified by flash chromatography
  7. washeluting with 3:7 ethyl acetate/hexane

出典と根拠

ORDレコード
ord-c5df0ed850d846b4afc945c4a59db9f0
出典データセット
uspto-grants-2010_08
特許番号
US07772366B2

反応ノート

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