Triethylamine → Methyl 2-({[4-(2,3-butadienyloxy)phenyl]sulfonyl}amino)-3-methylbutanoate

HRID 1180541Notes

Reaction equation

HRID 1180541 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[CH:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C(N(CC)CC)C.[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[CH:19]=[C:20]=[CH2:21]>>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:6][CH:5]([CH:7]([CH3:9])[CH3:8])[C:4]([O:3][CH3:2])=[O:10])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[CH:19]=[C:20]=[CH2:21]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 12498813Valine, methyl ester, hydrochloride (1:1)HCID 552804204-(2,3-Butadienyloxy)benzenesulfonyl chloride

Product 1

HCID 85826249Methyl 2-({[4-(2,3-butadienyloxy)phenyl]sulfonyl}amino)-3-methylbutanoateYield 87.6%

Procedure

To a solution of DL-valine methyl ester hydrochloride (527 mg, 3.15 mmol) was added triethylamine (579 mg, 5.72 mmol) followed by product from Example 5 (700 mg, 2.86 mmol) and the resulting mixture was stirred for 10 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 850 mg (87%) of the product as a solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c23d0fd5a7bc4c85a7f87e353f65a5f8
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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