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

HRID 2066172ノート

反応式

HRID 2066172 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19](C(O)=O)[CH:18]=2)=[CH:14][C:13]=1[F:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:31]([CH2:34]C)CC)C.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]>>[C:59]([O:63][C:34](=[O:43])[NH:31][C:19]1[CH:18]=[C:17]([O:16][C:15]2[CH:26]=[CH:27][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[C:13]([F:28])[CH:14]=2)[CH:22]=[CH:21][N:20]=1)([CH3:62])([CH3:61])[CH3:60]

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

To a suspension of 4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid (5.04 g) in tert-butanol (50 ml) was added triethylamine (4.6 ml) at room temperature, followed by stirring. Diphenylphosphoryl azide (3.13 ml) was added thereto at room temperature, followed by stirring under a nitrogen atmosphere at room temperature for 30 min. Then the reaction mixture was heated and stirred at 90° C. for 30 min and at 100° C. for 4 hr. The reaction mixture was allowed to cool down to room temperature. Ethyl acetate (25 ml) was added thereto, and the reaction mixture was stirred in an ice bath for 30 min. Precipitated crystals were collected by filtration and washed with diethyl ether. These crystals were dried under aeration at room temperature for 1 hr to provide the titled compound as colorless crystals (3.92 g, 65.5%).

後処理

  1. customat room temperature
  2. stirringby stirring under a nitrogen atmosphere at room temperature for 30 min
  3. temperatureThen the reaction mixture was heated
  4. stirringstirred at 90° C. for 30 min and at 100° C. for 4 hr
  5. stirringthe reaction mixture was stirred in an ice bath for 30 min
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washwashed with diethyl ether
  9. customThese crystals were dried under aeration at room temperature for 1 hr

出典と根拠

ORDレコード
ord-641ed045bf004a5bafac179b7340bc9d
出典データセット
uspto-grants-2012_10
特許番号
US08288538B2

反応ノート

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