Triethylamine → (R)-3-(2,5-difluoropyrimidin-4-yl)-4-((R)-1-fluoroethyl)oxazolidin-2-one

HRID 57368

反応式

HRID 57368 の反応式
[F:1][C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@@H:13](O)[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[C:5]([F:17])=[CH:4][N:3]=1.[F:18]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C>C1COCC1.O.CCOC(C)=O.CCCCCCC>[F:1][C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@H:13]([F:18])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[C:5]([F:17])=[CH:4][N:3]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 90417132(R)-3-(2,5-difluoropyrimidin-4-yl)-4-((S)-1-hydroxyethyl)oxazolidin-2-one

生成物 1

HCID 90415014(R)-3-(2,5-difluoropyrimidin-4-yl)-4-((R)-1-fluoroethyl)oxazolidin-2-one収率 32%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 21899848Ethylacetate heptane溶媒

実験手順

To a round bottom flask containing a solution of (R)-3-(2,5-difluoropyrimidin-4-yl)-4-((S)-1-hydroxyethyl)oxazolidin-2-one (0.47 g, 1.917 mmol) in THF (6.4 mL) was added perfluorobutanesulfonyl fluoride (1.03 mL, 5.75 mmol) followed by the addition of triethylamine trihydrofluoride (0.94 mL, 5.75 mmol) and triethylamine (2.40 mL, 17.3 mmol) resulting reaction mixture allowed to stir at room temperature for 6 hr. The reaction mixture was diluted with water and the aqueous mixture was extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 0 to 60%) provided a white crystalline of (R)-3-(2,5-difluoropyrimidin-4-yl)-4-((R)-1-fluoroethyl)oxazolidin-2-one (150 mg, 0.61 mmol, 32% yield). 1H NMR (400 MHz, CDCl3) δ 1.37 (dd, J=24.26, 6.26 Hz, 3H) 4.48 (dd, J=9.39, 4.70 Hz, 1H) 4.63 (t, J=8.80 Hz, 1H) 4.90-5.02 (m, 1H) 5.02-5.25 (m, 1H) 8.50 (s, 1H). LCMS m/z 248.0 (M+H)+, Rt 0.59 min.

後処理

  1. customresulting
  2. customreaction mixture
  3. extractionthe aqueous mixture was extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated onto silica gel

出典と根拠

ORDレコード
ord-92072bde9ea74ea099c5208bfacfbdc3
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

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