Water → 60924-38-1

HRID 222140Notes

Reaction equation

HRID 222140 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>CC(CC(C)C)=O.CCCCCCC>[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

7

Reactant 4

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

Product 1

HCID 7130748560924-38-1Yield 90.5%

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
21 °C

Procedure

Pleuromutilin (20.1 g) and triethylamine (6.86 g) in methylisobutyl ketone (0.21 L) were cooled to −10° C. Methane sulphonyl chloride (7.91 g) in methylisobutyl ketone (0.04 L) was added at −5 to −10° C. After 1 h water (0.12 L) was added and the mixture was warmed to 20-22° C. The phases were separated and the methylisobutyl ketone phase was washed successively with water (0.09 L) and 10% brine (0.05 L). The methylisobutyl ketone solution was concentrated by distillation under reduced pressure to leave a residue of 57.4 g. Heptane (0.06 L) was added to the residue at 76-78° C. to crystallize the title compound. Further heptane (0.04 L) was added, the mixture was cooled to −5 to −8° C. and stirred for 1 h. The title compound was filtered off, washed with chilled heptane/methylisobutyl ketone (3:1, 0.028 L) and dried at <40° C. to give 21.94 g, 90.5% yield.

Workup

  1. customThe phases were separated
  2. washthe methylisobutyl ketone phase was washed successively with water (0.09 L) and 10% brine (0.05 L)
  3. concentrationThe methylisobutyl ketone solution was concentrated by distillation under reduced pressure
  4. customto leave a residue of 57.4 g
  5. customto crystallize the title compound
  6. additionFurther heptane (0.04 L) was added
  7. temperaturethe mixture was cooled to −5 to −8° C.
  8. filtrationThe title compound was filtered off
  9. washwashed with chilled heptane/methylisobutyl ketone (3:1, 0.028 L)
  10. customdried at <40° C.
  11. customto give 21.94 g, 90.5% yield

Sources & evidence

ORD record
ord-3a40b87ad30f4dad844c24133184f72c
Source dataset
uspto-grants-2012_06
Patent number
US08207191B2

Reaction notes

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