Diisopropylethylamine → (S)-4-Benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one

HRID 1394748

반응식

HRID 1394748 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:18])[CH2:15][O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC.[CH3:45][Si:46]([CH3:77])([C:71]([CH3:76])([CH3:75])[CH:72]([CH3:74])[CH3:73])[O:47][C:48]1[CH:55]=[C:54]([O:56][CH2:57][CH2:58][C:59]2[N:60]=[C:61]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[O:62][C:63]=2[CH3:64])[CH:53]=[CH:52][C:49]=1[CH:50]=[O:51]>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:18])[C@@H:15]([O:16][CH3:17])[C@@H:50]([C:49]1[CH:52]=[CH:53][C:54]([O:56][CH2:57][CH2:58][C:59]2[N:60]=[C:61]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)[O:62][C:63]=2[CH3:64])=[CH:55][C:48]=1[O:47][Si:46]([CH3:77])([CH3:45])[C:71]([CH3:76])([CH3:75])[CH:72]([CH3:74])[CH3:73])[OH:51])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 10106101(S)-4-benzyl-3-(2-methoxyacetyl)oxazolidin-2-one2회HCID 222739052-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

생성물 1

HCID 69280419(S)-4-Benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

1.8 g (7.21 mmol) (S)-4-Benzyl-3-methoxyacetyl-oxazolidin-2-one (for the preparation of (S)-4-benzyl-3-methoxyacetyl-oxazolidin-2-one see: D. Hunziker, N. Wu, K. Kenoshita, D. E. Cane, C. Khosla, Tetrahedron Lett. 1999, 40, 635-638) were dissolved under an argon atmosphere in 10 ml CH2Cl2 and treated with 1.44 ml (8.42 mmol) Hünig's base. After cooling to −78° C., nBu2BOTf was added slowly (7.21 ml of 1M solution in CH2Cl2) and enolborinate formation allowed to proceed for 0.25 hours at −78° C. and for 1 hour at 0° C. After recooling to −78° C., a solution of 2.8 g (6 mmol) of 2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde in 10 ml CH2Cl2 was added via dropping funnel during 90 minutes and the mixture kept for 95 minutes at −78° C. and for one hour at 0° C. Pouring onto crashed ice, twofold extraction with AcOEt, washing with brine and water, drying over magnesium sulfate, and evaporation of the solvents, followed by chromatography (silica gel, heptane/AcOEt) left finally 2.905 g (67%) of the title compound as a yellow oil. According to 1H-NMR spectroscopy, one of the four isomers is strongly predominating. The configuration was tentatively assigned as 2S,3R according to D. Haigh et al., Tetrahedron: Asymmetry 1999, 10, 1353-1367.

후처리

  1. customAfter recooling to −78° C.
  2. customduring 90 minutes
  3. waitthe mixture kept for 95 minutes at −78° C. and for one hour at 0° C
  4. additionPouring
  5. extractionice, twofold extraction with AcOEt
  6. washwashing with brine and water
  7. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  8. waitleft finally 2.905 g (67%) of the title compound as a yellow oil

출처 및 근거

ORD 기록
ord-026860b52ad04027b4608a4a50c4a8db
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348349B2

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