Hydrochloric Acid → (1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl 4-methylbenzenesulfonate

HRID 1352868

반응식

HRID 1352868 반응식
[H-].[Na+].[N:3]1([C:9](=[O:13])[C@H:10]([OH:12])[CH3:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl>O1CCCC1.C(OCC)C>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:12][C@H:10]([CH3:11])[C:9]([N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[O:13])(=[O:22])=[O:21])=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 14978393(R)-2-Hydroxy-1-morpholinopropan-1-one

생성물 1

HCID 10903086(1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl 4-methylbenzenesulfonate수율 58%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of sodium hydride (60% in paraffin liquid) (8.41 g, 210 mmol) in tetrahydrofuran (120 ml was dropped (2R)-1-morpholin-4-yl-1-oxopropane-2-ol (32.1 g) in tetrahydrofuran (150 ml) under stirring, ice cooling and an atmosphere of nitrogen. The mixture was then stirred for 30 minutes at 50° C. After being ice-cooled, thereto was dropped a solution of p-toluenesulfonyl chloride (45.8 g, 234 mmol) in tetrahydrofuran (180 ml), and the mixture was stirred for 4 hours at room temperature. Thereto was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to give the oily residue. Thereto was added diethyl ether and the resulting precipitate was taken by filtration, washed with diethyl ether and dried under reduced pressure to give the subject compound as a white solid (36.1 g, 115 mmol, 58%).

후처리

  1. stirringThe mixture was then stirred for 30 minutes at 50° C
  2. temperaturecooled
  3. stirringthe mixture was stirred for 4 hours at room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialan aqueous saturated sodium chloride solution and dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto give the oily residue
  9. filtrationthe resulting precipitate was taken by filtration
  10. washwashed with diethyl ether
  11. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-64b89deb5db74bba958945d39af86b13
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220773B2

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