Acetone → 4-[(1-Carboxy-1-methylethyl)amino]-2-fluorobenzoic acid

HRID 705414

Reaction equation

HRID 705414 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.Cl[C:13](Cl)(Cl)[C:14]([CH3:17])(O)[CH3:15].[OH-:20].[Na+].CC(C)=[O:24]>>[C:13]([C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1)([CH3:17])[CH3:15])([OH:24])=[O:20]

Participants

5

Reactant 4

HCID 180AcetoneHCID 5977ChlorobutanolHCID 14798Sodium HydroxideHCID 3026804-Amino-2-fluorobenzoic acid

Product 1

HCID 673955034-[(1-Carboxy-1-methylethyl)amino]-2-fluorobenzoic acid

Conditions

Temperature
0 °C

Procedure

4-Amino-2-fluoro-benzoic acid (0.2 g, 1.29 mmol) and 1,1,1-trichloro-2-methyl-propan-2-ol (0.593 g, 3.35 mmol) were dissolved in anhydrous acetone and the solution was cooled at 0° C. Powdered sodium hydroxide (0.2 g, 5.01 mmol) was added portion-wise after which the reaction mixture was warmed to and stirred at room temperature for 12 h. Volatiles were removed under reduced pressure and the residue was acidified with 1M aqueous HCl. The crude product obtained was purified by reverse phase HPLC to obtain 4-(1-carboxy-1-methyl-ethylamino)-2-fluoro-benzoic acid.

Workup

  1. temperaturewas warmed to and
  2. customVolatiles were removed under reduced pressure
  3. customThe crude product obtained
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8de38b3b91444bbfa8ff00208485c8cd
Source dataset
uspto-grants-2015_11
Patent number
US09174943B2

Linked notes

Loading…