Hydrochloric Acid → HCID 4679772, compound

HRID 1726378Notes

Reaction equation

HRID 1726378 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11].Cl>CC(C)=O.[OH-].[Na+]>[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:1][CH:2]([CH3:3])[C:4]([OH:6])=[O:5])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 98082-Fluorobenzoyl chloride2×

Product 1

HCID 4679772HCID 4679772, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a homogeneous solution of L-alanine(5 g, 56.1 mmol) in acetone (90 ml) and 1N NaOH (90 ml) was added 2-fluorobenzoyl chloride (8.9 g, 56.1 mmol) dropwise. Basicity of the reaction was maintained by adding 1N NaOH periodically. After the addition of 2-fluorobenzoyl chloride was completed, the reaction mixture was acidified to pH 2 using 1N HCl. The oil that precipitated out was extracted into EtOAc, which was dried over MgSO4, filtered, and concentrated to yield 2-(2-fluorobenzoylamino)propionic acid (intermediate XXIa, 3.92 g). Upon standing, more crystals of intermediate XXIa (2.3 g) precipitated from the acidic aqueous solution and were collected.

Workup

  1. temperatureBasicity of the reaction was maintained
  2. customThe oil that precipitated out
  3. extractionwas extracted into EtOAc, which
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31877a24503245b588986c1daa739f11
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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