Tributylphosphine → 5(R)-[N-Isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)aminomethyl]-3-[3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one

HRID 1582329

반응식

HRID 1582329 반응식
[Cl:1][C:2]([Cl:14])([Cl:13])[CH2:3][O:4][C:5]([NH:7][C:8]1[CH:12]=[CH:11][O:10][N:9]=1)=[O:6].O[CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH2:34][CH2:33][N:32]([CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:31][CH:30]=3)=[C:25]([F:42])[CH:24]=2)[CH2:18]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[O:10]1[CH:11]=[CH:12][C:8]([N:7]([CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH2:34][CH2:33][N:32]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH2:31][CH:30]=4)=[C:25]([F:42])[CH:24]=3)[CH2:18]2)[C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:13])[Cl:14])=[O:6])=[N:9]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 12114192,2,2-Trichloroethyl isoxazol-3-ylcarbamateHCID 11668069(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-hydroxymethyl-oxazolidin-2-one

생성물 1

HCID 207256965(R)-[N-Isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)aminomethyl]-3-[3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (1.30 g, 5.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one (WO 97/30995; 1.91 g, 5.0. mmol) and tributylphosphine (1.52 g, 7.5 mmol) in dry tetrahydrofuran (50 ml) under a nitrogen atmosphere at 0° C., was added 1,1′-(azodicarbonyl)dipiperidine (1.89 g, 7.5 mmol) in dry tetrahydrofuran (15 ml). The solution was stirred at 0° C. for 30 minutes before being allowed to come to room temperature and it was then stirred for 2 days. The mixture was filtered, concentrated by rotary evaporation and chromatographed by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32-63), and triturated with ether to give the title compound as a white amorphous solid (1.62 g, 52%). NMR: 2.41 (m, 2H), 2.60 (t, 2H), 3.15 (m, 2H), 3.90 (dd, 1H), 4.18 (m, 2H), 4.37 (dd, 1H), 5.04 (dd, 3H), 5.95 (broad s, 1H), 6.88 (s, 1H), 7.32 (m, 3H), 8.89 (s, 1H); m/z ES+ (M+H)=623.

후처리

  1. customto come to room temperature
  2. stirringit was then stirred for 2 days
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated by rotary evaporation
  5. customchromatographed by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32-63)
  6. customtriturated with ether

출처 및 근거

ORD 기록
ord-ea7ac6aa2be7479d9393a2605e69b340
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

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