Triethylamine → methanesulfonic acid (R)-1-carbamoyl-ethyl ester

HRID 2044667Notes

Reaction equation

HRID 2044667 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C1COCC1.O>[C:3]([C@H:2]([O:1][S:15]([CH3:14])(=[O:17])=[O:16])[CH3:6])(=[O:4])[NH2:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1530236(2R)-2-hydroxypropanamide

Product 1

HCID 58205027methanesulfonic acid (R)-1-carbamoyl-ethyl esterYield 71,233.602%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, to a solution of (R)-2-hydroxy-propionamide (10 g, 0.11 mmol) and triethylamine (17.2 mL, 0.12 mmol) in THF (130 mL) at 0° C. was added dropwise, methanesulfonyl chloride (9.56 mL, 0.12 mmol) causing a thick white precipitate to form. The reaction mixture was stirred at RT for 2 hours. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was triturated with TBME to yield methanesulfonic acid (R)-1-carbamoyl-ethyl ester as a white solid (13.1 g, 70%). 1H NMR (400 MHz, d6-DMSO) 7.56 (1H, br s), 7.41 (1H, br s), 4.91 (1H, t, J=6.6 Hz), 3.23 (3H, s), 1.44 (3H, d, J=6.6 Hz)

Workup

  1. customto form
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was triturated with TBME

Sources & evidence

ORD record
ord-78f76905b7e94089a71cd4ca8a2ed9a7
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

Loading…