Triethylamine → Methyl 2-methanesulfonamido-3-methylbutanoate

HRID 1061677Notes

Reaction equation

HRID 1061677 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:17])[CH:12]([CH:14]([CH3:16])[CH3:15])[NH2:13].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(OCC)(=O)C>C(Cl)Cl>[CH3:18][S:19]([NH:13][CH:12]([CH:14]([CH3:16])[CH3:15])[C:11]([O:10][CH3:9])=[O:17])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 12498813Valine, methyl ester, hydrochloride (1:1)

Product 1

HCID 23199094Methyl 2-methanesulfonamido-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6.7 ml) is added to a solution of DL-valine methyl ester hydrochloride (3.35 g, Reference compound No. 45-1) in methylene chloride (70 ml). The mixture is cooled with ice, methanesulfonyl chloride (1.9 ml) is added to the mixture, and the whole is stirred overnight. Ethyl acetate is added to the reaction mixture, the whole is washed with 0.1 N hydrochloric acid and saturated brine successively, and the organic layer is dried over anhydrous magnesium sulfate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (4.00 g).

Workup

  1. additionis added to the mixture
  2. washthe whole is washed with 0.1 N hydrochloric acid and saturated brine successively
  3. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9cae214f13154121bfbffdbfa25f4029
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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