DL-valine → HCID 22644755, compound

HRID 2084844Notes

Reaction equation

HRID 2084844 reaction equation
[NH2:1][CH:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:17]#[C:18][CH3:19]>C1COCC1.O.C(OCC)(=O)C>[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:17]#[C:18][CH3:19]

Participants

6

Reactant 3

HCID 1182DL-valineHCID 8471TriethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 22644755HCID 22644755, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 0.500 g (4.255 mmol) D,L-valine in 40 mL of THF/water (1:1) was added 5.0 mL of triethylamine followed by 1.144 g (4.681 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride and the reaction was stirred overnight at room temperature. The reaction mixture was then diluted with ethyl acetate and the organic layer was washed with water and 5% HCl solution, dried over MgSO4, filtered and concentrated in vacuo. The solid residue was washed with ether/hexanes (1:1) to provide 0.383 g (28%) of the sulfonamide as a white solid. Electrospray Mass Spec 323.9 (M−H)−.

Workup

  1. washthe organic layer was washed with water and 5% HCl solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe solid residue was washed with ether/hexanes (1:1)

Sources & evidence

ORD record
ord-d97f73439bc44727a6c27a78b5787648
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

Loading…