tert-Butanol → Tert-butyl [4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridin-2-yl]carbamate

HRID 492844ノート

反応式

HRID 492844 の反応式
C([N:3]([CH2:6]C)CC)C.[CH2:8]([O:15][C:16]([NH:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26](C(O)=O)[CH:25]=2)=[CH:21][C:20]=1[F:35])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.C(OCC)(=O)C.[C:59]([OH:63])([CH3:62])([CH3:61])[CH3:60]>>[CH2:8]([O:15][C:16]([NH:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:3][C:6](=[O:43])[O:63][C:59]([CH3:62])([CH3:61])[CH3:60])[CH:25]=2)=[CH:21][C:20]=1[F:35])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 231530984-(4-Benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid

生成物 1

HCID 57677355Tert-butyl [4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridin-2-yl]carbamate収率 65.5%

実験手順

Triethylamine (4.6 ml) was added to a suspension of 4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid (5.04 g) in tert-butanol (50 ml) at room temperature, and the mixture was stirred. After adding diphenylphosphoryl azide (3.13 ml) thereto at room temperature, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere. It was then heated and stirred at 90° C. for 30 minutes and at 100° C. for 4 hours. The reaction mixture was subsequently cooled to room temperature. Ethyl acetate (25 ml) was added thereto, and the reaction mixture was stirred for 30 minutes while cooling in an ice bath. The precipitated crystals were filtered and washed with diethyl ether. They were then subjected to aeration drying for 1 hour at room temperature to provide the title compound (3.92 g, 65.5%) as colorless crystals.

後処理

  1. stirringat room temperature, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere
  2. temperatureIt was then heated
  3. stirringstirred at 90° C. for 30 minutes and at 100° C. for 4 hours
  4. stirringthe reaction mixture was stirred for 30 minutes
  5. temperaturewhile cooling in an ice bath
  6. filtrationThe precipitated crystals were filtered
  7. washwashed with diethyl ether
  8. customdrying for 1 hour at room temperature

出典と根拠

ORDレコード
ord-35b0b60eed054ae4a817432439b3c45e
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

読み込み中…