Tributylphosphine → (5S)-3-(3-fluoro-4-morpholino-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one

HRID 1582327

반응식

HRID 1582327 반응식
ClC(Cl)(Cl)CO[C:5]([NH:7][C:8]1[CH:12]=[CH:11][O:10][N:9]=1)=O.OC[C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[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]([NH:7][CH2:5][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[C:25]([F:35])[CH:24]=3)[CH2:18]2)=[N:9]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 12114192,2,2-Trichloroethyl isoxazol-3-ylcarbamateHCID 10541953(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

생성물 1

HCID 497405(5S)-3-(3-fluoro-4-morpholino-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one수율 331.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (260 mg, 1.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (see WO 95/07271; 293 mg, 1 mmol) and tributylphosphine (303 mg, 1.5 mmol) in dry tetrahydrofuran (10 ml) at 0° C. under a nitrogen atmosphere, was added 1,1′-(azodicarbonyl)dipiperidine (378.5 mg, 1.5 mmol) in dry tetrahydrofuran (3 ml). The reaction allowed to warm to room temperature and was stirred for 4 days by which time a white suspension had formed. The reaction mixture was filtered and the residue washed with tetrahydrofuran. The filtrate was reconcentrated by rotary evaporation to give a yellow oil (1.2 g) which was purified by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32-63) and further MPLC (100% CH2Cl2, ICN Alumina N 32-63). Concentration of the fractions by rotary evaporation gave the title compound as a crisp white foam (296 mg, 55%). NMR: 2.97 (t, 4H), 3.73 (t, 4H), 3.88 (m, 1H), 4.17 (m, 2H), 4.38 (m, 1H), 5.04 (m, 3H), 6.90 (s, 1H), 7.06 (t, 1H), 7.18(dd, 1H), 7.46 (dd, 1H), 8.91 (d, 1H); m/z ES+ (M+H)=537.

후처리

  1. customhad formed
  2. filtrationThe reaction mixture was filtered
  3. washthe residue washed with tetrahydrofuran
  4. customThe filtrate was reconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-f0e7a80146144d7c871483e3d4c4cf72
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

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