Hydroxylamine → Cgs-27023

HRID 1720623

반응식

HRID 1720623 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

HCID 446504Cgs-27023

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-07c3c8f519d84388888876209ab9ee21
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506242

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