Acetic Anhydride → 9-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-acetoxy-5-oxotetrahydrofuran-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

HRID 2230478ノート

反応式

HRID 2230478 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.[CH3:33][C:34](OC(C)=O)=[O:35].OS([O-])(=O)=O.[Na+]>N1C=CC=CC=1>[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][C:34](=[O:35])[CH3:33])=[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 7918Acetic AnhydrideHCID 516919Sodium BisulfateHCID 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 184656979-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-acetoxy-5-oxotetrahydrofuran-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide収率 37.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 214e (287 mg, 0.65 mmol) in pyridine (5 mL) was treated with Ac2O (0.4 mL, 3.62 mmol). After 6 hours, the reaction mixture was poured into 5% NaHSO4 and extracted 3 times with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Chromatography (SiO2, EtOAc) afforded 119 mg of 2100h, 1HNMR (CDCl3, mixture of four diastereoisomers) δ1.80-2.05(m), 2.12(s), 2.13(s), 2.19(s), 2.22(d), 2.67-2.75(m), 2.80-2.95(m), 3.00-3.20(m), 3.21-3.33(m), 3.50-3.95(four discrete multiplets), 4.19(m), 4.55(m), 4.57-4.65(m), 4.69(m), 4.85-4.95(m), 5.04(m), 5.10(s), 5.10-5.22(m), 6.46(d), 6.03(s), 6.50(d), 6.58(d), 6.75(d), 6.95-7.05(m), 7.22(m), 7.30(m), 7.71(d), 7.75-7.83(m).

後処理

  1. extractionextracted 3 times with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2f50df8a31bc47efa872e302b3198ab0
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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