Water → HCID 86609961, compound

HRID 1272076Notes

Reaction equation

HRID 1272076 reaction equation
CS(Cl)(=O)=O.[CH3:6][C:7]([NH:14][S:15]([CH2:18][CH:19](O)[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:17])=[O:16])([CH3:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.O>ClCCl>[CH3:13][C:7]([NH:14][S:15](/[CH:18]=[CH:19]/[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:17])=[O:16])([CH3:6])[CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866099602-Hydroxy-2-pyridin-3-yl-ethanesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

Product 1

HCID 86609961HCID 86609961, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (2.1 mL, 27 mmol) in dichloromethane (10 mL) was added dropwise over 15 minutes to a solution of 2-hydroxy-2-pyridin-3-yl-ethanesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.67 g, 18 mmol) and triethylamine (15 mL, 108 mmol) in dichloromethane (40 mL) at 0° C. The mixture was warmed to ambient temperature and stirred for a further 1 hour. Water (50 mL) was added in one portion to the reaction mixture and the whole was extracted with dichloromethane (2×50 mL). The organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, ethyl acetate:heptane 1:1 to ethyl acetate) to afford (E)-2-pyridin-3-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide as a pale yellow solid (3.91 g, 73%).

Workup

  1. extractionthe whole was extracted with dichloromethane (2×50 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, ethyl acetate:heptane 1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-9b5035423cf24e9d865638002ff9ac87
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

Loading…