Triphenylphosphine → (5R)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167462

반응식

HRID 1167462 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[O:15][C:14]2=[O:20])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.O[C:22]1[CH:26]=[CH:25][O:24][N:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][O:19][C:22]3[CH:26]=[CH:25][O:24][N:23]=3)[O:15][C:14]2=[O:20])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 104927643-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-oneHCID 178516613HCID 178516613, 화합물

생성물 1

HCID 497412(5R)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one수율 59.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (WO 96/23788; 280 mg, 1 mmol), 3-hydroxyisoxazole (94 mg, 1.1 mmol), and triphenylphosphine (330 mg, 1.25 mmol) were suspended by stirring in dry tetrahydrofuran (10 ml) under nitrogen at ambient temperature. Diisopropylazodicarboxylate (308 mg, 1.5 mmol) was added dropwise over 10 minutes. The suspension dissolved, and stirring was continued at the same temperature for 2 hours. The mixture was evaporated to dryness, and the residue purified by chromatography on a 20 g silica Mega Bond Elut® columns, eluting with a gradient increasing in polarity from 50 to 100% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the desired product (206 mg). MS (ESP): 345 (MH+) for C16H13FN4O4.

후처리

  1. dissolutionThe suspension dissolved
  2. customThe mixture was evaporated to dryness
  3. customthe residue purified by chromatography on a 20 g silica Mega Bond Elut® columns
  4. washeluting with
  5. temperaturea gradient increasing in polarity from 50 to 100% EtOAc in isohexane
  6. customevaporated

출처 및 근거

ORD 기록
ord-b3b6251e19af4ef2a1c434e00097a7ce
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617339B1

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