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

HRID 1031585ノート

反応式

HRID 1031585 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6a494691686c46eaaa010e5173ab74f3
出典データセット
uspto-grants-1990_09
特許番号
US04954507

反応ノート

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