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

HRID 553694ノート

反応式

HRID 553694 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][C:3]=1[CH3:17].C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([OH:51])[CH3:50]>C1(C)C=CC=CC=1>[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([O:51][C:23](=[O:32])[NH:20][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:17])[CH:4]=1)[CH3:50]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2779054(R)-1-(2-Fluorophenyl)ethanolHCID 585394455-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazole-4-carboxylic acid

生成物 1

HCID 54765945[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl Ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1.78 g, 6.0 mmol) was dissolved in toluene (50 mL). Triethylamine (0.92 mL, 6.6 mmol) was added, followed by diphenylphosphoryl azide (1.43 mL, 6.6 mmol), and the mixture was stirred for 10 minutes. (R)-1-(2-Fluoro-phenyl)-ethanol (0.924 g, 6.6 mmol) was added, and the reaction was stirred at 85° C. for 3 hours, and then overnight at room temperature. The mixture was concentrated, and the residue was diluted with dichloromethane and purified by silica gel chromatography to give the title compound.

後処理

  1. stirringthe reaction was stirred at 85° C. for 3 hours
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with dichloromethane
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-f21cadbf42b94d24b60cdd5232437602
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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