Ammonium formate → tert-Butyl-3-aminobenzoate

HRID 963083

反応式

HRID 963083 の反応式
C(OC([NH:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 19085317tert-Butyl 3-(N-benzyloxycarbonylamino)benzoate

生成物 1

HCID 2737408tert-Butyl-3-aminobenzoate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

tert-Butyl 3-(N-benzyloxycarbonylamino)benzoate (2.18 g) and ammonium formate (2.1 g) were dissolved in methanol (30 ml). Catalyst (1 g) of 10% palladium/carbon was added, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was filtered through Celite to remove catalyst and the filtrate was concentrated. The residue was partitioned between chloroform and water. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give tert-butyl 3-aminobenzoate. This compound was dissolved in tetrahydrofuran (30 ml). N,N'-Carbonyldiimidazole (1.05 g) was added, and the mixture was stirred at room temperature for 3 hours. Triethylamine (1.82 ml) and 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate (4.82 g) were added to the reaction mixture, and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated. The residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and methanol (10:1) as an eluent, and crystallized from isopropyl ether to give 0.95 g of tert-butyl 3-(3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)ureido)benzoate.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove catalyst
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between chloroform and water
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fef1ac21ed8c4fa483adfdd70b95f117
出典データセット
uspto-grants-1998_06
特許番号
US05760032

関連ノート

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