p-Toluenesulfonic acid → 9-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-isopropoxy-5-oxo-tetrahydro-furan-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

HRID 1532913ノート

反応式

HRID 1532913 の反応式
[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]([CH:30]=[O:31])[CH2:26][C:27]([OH:29])=[O:28])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:32])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]1(C)[CH:38]=CC(S(O)(=O)=O)=C[CH:34]=1.C([O-])(O)=O.[Na+]>C(O)(C)C>[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]3[CH2:26][C:27](=[O:29])[O:28][CH:30]3[O:31][CH:33]([CH3:38])[CH3:34])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:32])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 184657033-(9-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamido)-4-oxobutanoic acid

生成物 1

HCID 184657169-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-isopropoxy-5-oxo-tetrahydro-furan-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide収率 198.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 214e (101 mg, 0.23 mmol) in isopropanol (10 ml) was stirred at room temperature with a catalytic amount of p-toluenesulfonic acid (10 mg). After 75 minutes, the reaction mixture was poured into saturated NaHCO3 and extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated. Flash chromatography (SiO2, CH2CHl2to EtOAc) afforded 56 mg (51%) of 2100a as a white solid: 1H NMR (CDCl3; mixture of diastereomers) δ 7.9-7.8 (2H,m), 7.6-7.5 (1H, m), 7.5-7.4 (2H, m), 7.1 (0.5H, d), 6.9 (0.5H, d), 6.4 (0.5H,d), 5.6 (0.5H, d), 5.3 (0.5H, s), 5.2-5.1 (1H, m), 4.95 (0.5H, m), 4.75-4.5 (1.5H, m), 4.35 (0.5H, t), 4.1 (0.5H, m), 3.98 (0.5H, m), 3.3-2.75 (4H, m), 2.5-2.4 (2H,m), 2.25 (1H, m), 2.1-1.9 (3H,m) 1.75-1.55 (2H,m).

後処理

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-47d8133ea9f0456b8b44c66be4ee0348
出典データセット
uspto-grants-2001_03
特許番号
US06204261B1

反応ノート

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