Triethylamine → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester

HRID 553684ノート

反応式

HRID 553684 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[F:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([OH:46])[CH3:45]>C1(C)C=CC=CC=1>[F:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([O:46][C:22](=[O:31])[NH:19][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:45]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 1230662-Fluoro-alpha-methylbenzenemethanolHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

生成物 1

HCID 67352942[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (4 g, 14.2 mmol) was dissolved in toluene (150 mL). Triethylamine (2.187 mL, 15.6 mmol) was added, followed by diphenylphosphoryl azide (3.372 mL, 15.6 mmol), and the mixture was stirred for 10 minutes. 2-Fluoro-alpha-methylbenzyl alcohol (2 g, 15.6 mmol) was added, and the reaction was stirred at 80° C. overnight. The mixture was cooled to room temperature and concentrated, and the residue was partitioned between with EtOAc and water. The organic layer was washed 4 times with water and once with brine, and then dried, filtered, and concentrated, and the residue was purified by silica gel chromatography (dry load; 0-100% EtOAc in hexanes) to give [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester.

後処理

  1. stirringthe reaction was stirred at 80° C. overnight
  2. concentrationconcentrated
  3. customthe residue was partitioned between with EtOAc and water
  4. washThe organic layer was washed 4 times with water
  5. dry with materialonce with brine, and then dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography (dry load; 0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-dfb13a6b993e49309c164033a2866377
出典データセット
uspto-grants-2011_11
特許番号
US08048902B2

反応ノート

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