Methanesulfonic Acid → HCID 18318088, compound

HRID 1700256Notes

Reaction equation

HRID 1700256 reaction equation
CS(O)(=O)=O.C([N:13]1[CH2:18][CH2:17][C:16]([C:24]2(O)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1)(OC(C)(C)C)=O.[OH-].[Na+]>O>[O:27]1[CH2:28][CH2:29][C:24]([C:16]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14][NH:13][CH2:18][CH2:17]2)=[CH:25][CH2:26]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 18318103HCID 18318103, compound

Product 1

HCID 18318088HCID 18318088, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Methanesulfonic acid (1.48 gm; 15.4 mmol) was add to the alcohol of Step A (1.07 gm; 2.99 mmol) in TMF at 0° C. The reaction mixture was then warmed to 60° C. and stirred overnight. Water was added and 1N NaOH was added until mixture turned to basic. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with brine and then dried over magnesium sulfate, filtered and then concentrated to give 0.47 gm of the title compound.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7d8217d73d64e5bbba28027ec057608
Source dataset
uspto-grants-2002_02
Patent number
US06350760B1

Reaction notes

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