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

HRID 2045834ノート

反応式

HRID 2045834 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12](C(O)=O)=[C:11]([CH3:16])[O:10][N:9]=2)=[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:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C@H:48]([OH:50])[CH3:49]>C1(C)C=CC=CC=1>[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C@H:48]([O:50][C:22](=[O:31])[NH:19][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N:9][O:10][C:11]=1[CH3:16])[CH3:49]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2779054(R)-1-(2-Fluorophenyl)ethanolHCID 223091073-(4-Bromophenyl)-5-methylisoxazole-4-carboxylic acid

生成物 1

HCID 68184602[3-(4-Bromo-phenyl)-5-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-(4-bromophenyl)-5-methylisoxazole-4-carboxylic acid (0.100 g, 0.35 mmol) in toluene (3 mL) was added triethylamine (0.054 mL, 0.39 mmol) and diphenylphosphoryl azide (0.084 mL, 0.39 mmol), followed by (R)-1-(2-fluoro-phenyl)-ethanol (0.055 g, 0.39 mmol), and the reaction was stirred at 80° C. for 1 hour. Once no starting material was seen by analytical LCMS, standard aqueous work-up was performed. The organic layer was treated with silica gel, and the mixture was concentrated and purified by silica gel chromatography to give the title compound.

後処理

  1. additionThe organic layer was treated with silica gel
  2. concentrationthe mixture was concentrated
  3. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-7eaf8b10f6bf49cf870e164d6581df2c
出典データセット
uspto-grants-2013_11
特許番号
US08592402B2

反応ノート

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