Methanesulfonic Acid → HCID 68552740, compound

HRID 1951989Notes

Reaction equation

HRID 1951989 reaction equation
CO[C:3](OC)([CH3:5])[CH3:4].CS(O)(=O)=O.[Cl:13][CH2:14][C@@H:15]([OH:29])[CH2:16][C@@H:17]([OH:28])[CH2:18][C:19]([N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[O:20]>CC(C)=O>[Cl:13][CH2:14][C@H:15]1[O:29][C:3]([CH3:5])([CH3:4])[O:28][C@@H:17]([CH2:18][C:19]([N:21]([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:27])[CH3:26])=[O:20])[CH2:16]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 64952,2-DimethoxypropaneHCID 86639761HCID 86639761, compound

Product 1

HCID 68552740HCID 68552740, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

2,2-dimethoxy propane (1050 ml) and 2.6 ml of methane sulfonic acid added to a solution of 280 grams of (3R,5S)-6-chloro-3,5-dihydroxy-N,N-diisopropylhexanamide, 1500 ml of acetone. Stirred the reaction mixture for 3 hours at 25-35° C. Quenched the reaction mixture with sodium bicarbonate solution. Separated the organic and inorganic phases. Extracted the aqueous layer with petroleum ether and washed the organic layer with brine solution. Dried the organic layer over sodium sulfate. Distilled the solvent completely under reduced pressure to get the title compound as a residue.

Workup

  1. customQuenched the reaction mixture with sodium bicarbonate solution
  2. customSeparated the organic and inorganic phases
  3. extractionExtracted the aqueous layer with petroleum ether
  4. washwashed the organic layer with brine solution
  5. dry with materialDried the organic layer over sodium sulfate
  6. distillationDistilled the solvent completely under reduced pressure

Sources & evidence

ORD record
ord-d5cc781a25d7494398fff9d234f42c2a
Source dataset
uspto-grants-2013_03
Patent number
US08404841B2

Reaction notes

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