Methanesulfonamide → HCID 67831691, compound

HRID 466913Notes

Reaction equation

HRID 466913 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][CH:12]([CH3:16])[C:13](O)=[O:14])[N:4]=1.[CH3:17][S:18]([NH2:21])(=[O:20])=[O:19].N12CCCN=C1CCCCC2>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][CH:12]([CH3:16])[C:13]([NH:21][S:18]([CH3:17])(=[O:20])=[O:19])=[O:14])[N:4]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14853399HCID 14853399, compound

Product 1

HCID 67831691HCID 67831691, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1,1-carbonyldiimidazole (1.70 g, 0.0105 mol) in dry tetrahydrofuran (130 ml), 2-(4,6-dimethoxypyrimidin-2-yl)oxypropionic acid (2.28 g, 0.01 mol), prepared as described in Example 1(b) above, in tetrahydrofuran (30 ml) was added dropwise at room temperature (~20° C.). The solution was refluxed for 1/2 hour and allowed to cool. Methanesulphonamide (0.95 g, 0.01 mol) was added in one solid portion and the mixture stirred for 15 minutes before 1,8-diazabicyclo[5.4.0]undec-7-ene (1.52 g, 0.01 mol) in tetrahydrofuran (30 ml) was added dropwise at room temperature (~20° C.). After a short duration the tetrahydrofuran was removed and the residue acidified with IM hydrochloric acid solution. The product was extracted with chloroform, backwashed with water and dried. The solvent was removed and the product purified on silica gel eluting with 3% by volume methanol/chloroform to yield the title compound as a solid (1.79 g).

Workup

  1. additionwas added dropwise at room temperature (~20° C.)
  2. temperatureThe solution was refluxed for 1/2 hour
  3. temperatureto cool
  4. additionwas added dropwise at room temperature (~20° C.)
  5. customAfter a short duration the tetrahydrofuran was removed
  6. extractionThe product was extracted with chloroform
  7. customdried
  8. customThe solvent was removed
  9. customthe product purified on silica gel eluting with 3% by volume methanol/chloroform

Sources & evidence

ORD record
ord-e44d0f8767de49e9a1565e972c554ae3
Source dataset
uspto-grants-1992_10
Patent number
US05158599

Reaction notes

Loading…