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

HRID 2092440노트

반응식

HRID 2092440 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f9856a0c813e4a3c9e8b2b9c62c56303
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440707B2

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