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

HRID 2045834노트

반응식

HRID 2045834 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7eaf8b10f6bf49cf870e164d6581df2c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592402B2

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