Water → 60924-38-1

HRID 222139Notes

Reaction equation

HRID 222139 reaction equation
[CH3:1][C@H:2]1[C@@:11]2([CH3:27])[C@H:12]([O:22][C:23]([CH2:25][OH:26])=[O:24])[CH2:13][C@:14]([CH:20]=[CH2:21])([CH3:19])[C@@H:15]([OH:18])[C@H:16]([CH3:17])[C@:5]3([C@@H:10]2[C:8](=[O:9])[CH2:7][CH2:6]3)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].O>ClCCl>[CH3:1][C@H:2]1[C@:11]2([CH3:27])[C@@H:12]([O:22][C:23]([CH2:25][O:26][S:36]([CH3:35])(=[O:38])=[O:37])=[O:24])[CH2:13][C@@:14]([CH:20]=[CH2:21])([CH3:19])[C@H:15]([OH:18])[C@@H:16]([CH3:17])[C@@:5]3([C@@H:10]2[C:8](=[O:9])[CH2:7][CH2:6]3)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21724548HCID 21724548, compound

Product 1

HCID 7130748560924-38-1Yield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
17.5 °C

Procedure

Pleuromutilin (69.95 g at 90% purity) and triethylamine (26 mL, 18.33 g) in dichloromethane (0.55 L) were cooled to −10° C. Methane sulphonyl chloride (14.5 mL, 20.87 g) in dichloromethane (0.12 L) was added over 0.5 h at −5 to −10° C. After 0.5 h the mixture was warmed to 15-20° C. and water (0.25 L) added. The phases were separated and the aqueous phase was further extracted with dichloromethane (0.06 L). The combined dichloromethane solution was concentrated by distillation collecting 0.5 L. The distillation was continued by slowly adding propan-2-ol (0.3 L) and collecting a further 0.3 L to reach a solution temperature of 78° C. n-Heptane (0.29 L) was added slowly whilst maintaining the temperature between 75-80° C. The solution became turbid with the product crystallizing. The mixture was cooled to 0° C. and stirred for 1 h. The product was filtered off, washed with chilled 2:1 n-heptane/propan-2-ol (0.075 L) and dried under vacuum to give the title compound (75.33 g, 95.6%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was further extracted with dichloromethane (0.06 L)
  3. concentrationThe combined dichloromethane solution was concentrated by distillation
  4. customcollecting 0.5 L
  5. distillationThe distillation
  6. customcollecting a further 0.3 L
  7. customa solution temperature of 78° C. n-Heptane (0.29 L)
  8. additionwas added slowly
  9. temperaturewhilst maintaining the temperature between 75-80° C
  10. customcrystallizing
  11. temperatureThe mixture was cooled to 0° C.
  12. filtrationThe product was filtered off
  13. washwashed
  14. temperaturewith chilled 2:1 n-heptane/propan-2-ol (0.075 L)
  15. customdried under vacuum

Sources & evidence

ORD record
ord-19ce2bab9f1940e5a958cfaef69cbdd2
Source dataset
uspto-grants-2012_06
Patent number
US08207191B2

Reaction notes

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