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

HRID 705414

反応式

HRID 705414 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8de38b3b91444bbfa8ff00208485c8cd
出典データセット
uspto-grants-2015_11
特許番号
US09174943B2

関連ノート

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