Sodium triacetoxyborohydride → 6-[(4S)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847014ノート

反応式

HRID 1847014 の反応式
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=3[N:16]=2)[C:4](=[O:18])[CH2:3]1.[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([N:25]=[CH:26][C:27](=[O:35])[N:28]2[CH2:31][CH2:32][CH:33]=O)=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([N:25]=[CH:26][C:27](=[O:35])[N:28]2[CH2:31][CH2:32][CH2:33][NH:1][C@@H:2]2[CH2:6][N:5]([C:7]3[CH:8]=[CH:9][C:10]4[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=4[N:16]=3)[C:4](=[O:18])[CH2:3]2)=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 867249283-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propanalHCID 867249446-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

生成物 1

HCID 601616426-[(4S)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one収率 32%

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

6-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (94.1 mg, 0.379 mol) and 3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal (Reference Example 8; 106 mg, 0.456 mmol) were dissolved in chloroform/methanol (10:1, v/v, 6 ml). Molecular sieve 3 A (powder, 1.0 g) was added to the solution and heated under reflux for 3 hours. After cooling, sodium triacetoxyborohydride (145 mg, 0.684 mmol) was added to the reaction mixture and the mixture was stirred overnight at room temperature. After completion of the reaction, the molecular sieve was removed by filtration and a saturated sodium hydrogen carbonate aqueous solution was added to the filtrate and stirred. After separating the organic layer, the aqueous layer was extracted twice with chloroform/methanol (10:1, v/v) and combined with the organic layer. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by thin-layer chromatography (chloroform/methanol) to yield 56 mg (32%) of the title compound in the form of a colorless solid.

後処理

  1. additionMolecular sieve 3 A (powder, 1.0 g) was added to the solution
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. customAfter completion of the reaction
  6. customthe molecular sieve was removed by filtration
  7. additiona saturated sodium hydrogen carbonate aqueous solution was added to the filtrate
  8. stirringstirred
  9. customAfter separating the organic layer
  10. extractionthe aqueous layer was extracted twice with chloroform/methanol (10:1
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe obtained residue was purified by thin-layer chromatography (chloroform/methanol)

出典と根拠

ORDレコード
ord-fe5e929efae44f66a1ce69e28aa8a645
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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