Methanesulfonyl chloride → 1060801-28-6

HRID 520496Notes

Reaction equation

HRID 520496 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.C(N(C(C)C)CC)(C)C.CS([Cl:30])(=O)=O>C1COCC1>[Cl:30][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Product 1

HCID 679931361060801-28-6Yield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate 116 (85.0 g, 379 mmol) and diisopropylethylamine (296 g, 2.27 mol) in THF (850 mL) was added methanesulfonyl chloride (130 g, 1.14 mol) over a period of 30 min at 0° C. The mixture was stirred for 12 h at room temperature then washed with H2O (2×100 mL) and dried over Na2SO4. The mixture was concentrated and the crude residue was purified by flash chromatography (petroleum ether: ethyl acetate=10:1) to give 117 (30 g, 63% yield).

Workup

  1. washthen washed with H2O (2×100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationThe mixture was concentrated
  4. customthe crude residue was purified by flash chromatography (petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-47f2c440dc2341f1908de76ccb927349
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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