Hydrochloric Acid → ((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

HRID 1031585노트

반응식

HRID 1031585 반응식
[OH:1][CH:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[C@@H:4]([CH2:17][OH:18])[CH2:3]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[C:13]1([CH3:16])[CH:14]=[CH:15][C:10]([S:7]([N:5]2[CH2:6][C@@H:2]([O:1][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:3][C@@H:4]2[CH2:17][O:18][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])(=[O:9])=[O:8])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 156292684-Hydroxy-1-(4-toluenesulfonyl)-D-prolinol

생성물 1

HCID 15629272((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate수율 86%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
10 °C

실험 절차

To an ice-cold solution of 219.2 g (0.808 mole) of 2R, 4S-1-(4-toluenesulfonyl)-2-hydroxymethyl-4-hydroxy-pyrrolidine (6) in 1 L of pyridine were added 539.2 g (2.828 mole) of 4-toluenesulfonyl chloride in one portion. The temperature rose to 50° C. The mixture was cooled at 10° C. and kept for 2 hours at this temperature and then at room temperature overnight. The mixture was pured into 5 L of 2.4N hydrochloric acid. After cooling, a precipitate was collected, washed with cold water, dried under reduced pressure. This presicpitate was taken up with 1 L of ethanol, filtered and washed with cold ethanol, dried under reduce pressure to give 406 g (86%) of the titled compound. M.P. =134° C. [α]D =+57.13° (c=1.9, acetone).

후처리

  1. customrose to 50° C
  2. customat room temperature
  3. customovernight
  4. temperatureAfter cooling
  5. customa precipitate was collected
  6. washwashed with cold water
  7. customdried under reduced pressure
  8. filtrationfiltered
  9. washwashed with cold ethanol
  10. customdried

출처 및 근거

ORD 기록
ord-6a494691686c46eaaa010e5173ab74f3
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04954507

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