Hydrochloric Acid → 2-benzamido-3-methylbut-2-enoic acid

HRID 1016119Notes

Reaction equation

HRID 1016119 reaction equation
F[C:2]([CH3:9])([CH3:8])[CH:3]([C:5]([OH:7])=[O:6])[NH2:4].C([O-])(O)=O.[Na+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(OCC)(=O)C>[C:15]([NH:4][C:3](=[C:2]([CH3:9])[CH3:8])[C:5]([OH:7])=[O:6])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 3388873-Fluoro-DL-valineHCID 516892Sodium Bicarbonate

Product 1

HCID 558432-benzamido-3-methylbut-2-enoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-fluoro-DL-valine (165 mg, 1 mmol) in ethyl acetate (10 mL) was added NaHCO3 (sat. aq., 5 mL) followed by benzoyl chloride (1 mmol). The solution was stirred for 4 h, acidified with 1N HCl, and then extracted into ethyl acetate. The organic extracts were dried over MgSO4, filtered and concentrated to provide the crude 2-benzamido-3-methylbut-2-enoic acid.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a3ef78485294145aadf92f834bfdcdf
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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