Water → 2-Acetylamino-4-methanesulfonyloxymethylpyridine

HRID 1984710Notes

Reaction equation

HRID 1984710 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([NH:16][C:17]1[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][N:18]=1)(=[O:15])[CH3:14].O>O1CCCC1>[C:13]([NH:16][C:17]1[CH:22]=[C:21]([CH2:23][O:24][S:9]([CH3:8])(=[O:11])=[O:10])[CH:20]=[CH:19][N:18]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23151114N-(4-(hydroxymethyl)pyridin-2-yl)acetamide

Product 1

HCID 231510342-Acetylamino-4-methanesulfonyloxymethylpyridineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triethylamine (1.7 mL, 12 mmol) and methanesulfonyl chloride (0.70 mL, 9.0 mmol) in anhydrous tetrahydrofuran (3.0 mL) was added to a solution of (2-acetylaminopyridin-4-yl)methanol (Reference compound No. 12-1, 1.0 g, 6.0 mmol) in anhydrous tetrahydrofuran (9.0 mL) under ice-cooling, and the mixture was stirred for 20 minutes. Water (30 mL) was added to the reaction mixture, the whole was extracted with ethyl acetate (40 mL) three times, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting solid was filtered off with hexane. The solid was dried under reduced pressure at 40° C. to give 1.3 g of the title reference compound as a pale yellow solid. (Yield 87%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (40 mL) three times
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe resulting solid was filtered off with hexane
  5. customThe solid was dried under reduced pressure at 40° C.
  6. customto give 1.3 g of the title reference compound as a pale yellow solid

Sources & evidence

ORD record
ord-aadaa508f2b74bc1a956ff5a6c05eb4a
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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