Hydroxylamine → Cgs-27023

HRID 264327ノート

反応式

HRID 264327 の反応式
C(Cl)(=O)C(Cl)=O.Cl.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[C@H:20]([CH:24]([CH3:26])[CH3:25])[C:21](O)=[O:22])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[NH2:34][OH:35]>C(Cl)Cl.CN(C)C=O.O1CCCC1>[OH:35][NH:34][C:21](=[O:22])[C@H:20]([N:19]([S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[CH:24]([CH3:26])[CH3:25]

参加物

7

反応物 3

HCID 787HydroxylamineHCID 65578Oxalyl chlorideHCID 700617032(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

生成物 1

HCID 446504Cgs-27023

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Oxalyl chloride (106 mL, 1.22 mol) is added over 1 hour to dimethylformamide (92 mL) in methylene chloride (1250 mL) at 0° C. To this is added a solution of 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoic acid hydrochloride (248 g, 0.6 mol) in dimethylformamide (450 mL) over 1 hour, maintaining the temperature at 0° C. This solution is stirred an additional 2 hours at room temperature, and then added dropwise to a mixture of hydroxylamine (460 g of a 50% aqueous solution, 6.82 mol) in tetrahydrofuran (2400 mL). The reaction is stirred an additional 3 hours at 5° C., and then at room temperature overnight. The reaction mixture is filtered, the organic layer is collected, and the solvent is evaporated. The crude product is re-dissolved in methylene chloride (2 L), washed with water (2×1 L), saturated sodium bicarbonate (4×1 L), brine (1 L), dried (Na2SO4), and the solvent is evaporated. The product is dissolved in ethyl acetate (700 mL) and diluted with ether (1400 mL) to induce precipitation. The pure product is collected by filtration to provide N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide. After conversion to the hydrochloride salt, a white solid is obtained, m.p. 169°-170° C. (dec).

後処理

  1. stirringThe reaction is stirred an additional 3 hours at 5° C.
  2. customat room temperature
  3. customovernight
  4. filtrationThe reaction mixture is filtered
  5. customthe organic layer is collected
  6. customthe solvent is evaporated
  7. dissolutionThe crude product is re-dissolved in methylene chloride (2 L)
  8. washwashed with water (2×1 L), saturated sodium bicarbonate (4×1 L), brine (1 L)
  9. dry with materialdried (Na2SO4)
  10. customthe solvent is evaporated
  11. dissolutionThe product is dissolved in ethyl acetate (700 mL)
  12. additiondiluted with ether (1400 mL)
  13. customprecipitation
  14. filtrationThe pure product is collected by filtration

出典と根拠

ORDレコード
ord-be5b10ae50b4423181aee971537b4a41
出典データセット
uspto-grants-1997_07
特許番号
US05646167

反応ノート

読み込み中…