Potassium Hydroxide → (S)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

HRID 539098ノート

反応式

HRID 539098 の反応式
Cl.Cl.[NH2:3][C@@H:4]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][N:8]=1)[CH2:5][OH:6].[OH-].[K+].[C:16](=O)(OC(Cl)(Cl)Cl)[O:17]C(Cl)(Cl)Cl.[OH-].[Na+]>O.C(OCC)(=O)C.C1COCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:4]2[CH2:5][O:6][C:16](=[O:17])[NH:3]2)=[N:8][CH:9]=1

参加物

8

反応物 4

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 67033052(S)-2-Amino-2-(5-fluoropyridin-2-yl)ethan-1-ol dihydrochloride

生成物 1

HCID 67033294(S)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one収率 55.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To the solution of (S)-2-amino-2-(5-fluoropyridin-2-yl)ethanol bis-hydrochloride (9.8 g, 43 mmol) in water (200 mL) cooled to 0° C. was added potassium hydroxide (24 g, 430 mmol) followed by THF (200 mL) and the reaction stirred until the temperature reached 0° C. To the reaction was added bis(trichloromethyl) carbonate (13 g, 43 mmol) (in THF, 200 mL) dropwise such that the internal temperature did not exceed 7° C., and the reaction was stirred for 2 hours. The reaction was diluted with ethyl acetate and the aqueous layer made basic with NaOH (1M). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was chromatographed using a gradient of 50% DCM/EtOAc to EtOAc as eluent to yield (S)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (4.3 g, 24 mmol, 55% yield).

後処理

  1. customreached 0° C
  2. customdid not exceed 7° C.
  3. stirringthe reaction was stirred for 2 hours
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was chromatographed

出典と根拠

ORDレコード
ord-99a7f2385dca40699c4a1f952f12eb87
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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