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 2230475ノート

反応式

HRID 2230475 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, CH2Cl2 to EtOAc) afforded 56 mg (51%) of 2100a as a white solid: 1H NMR (CDCl3; mixture of diastereomers) δ7.9-7.8 (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-72b1bf6a623544cc9701ab4fb9d9b151
出典データセット
uspto-grants-2002_07
特許番号
US06423840B1

反応ノート

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