Potassium Carbonate → HCID 25018649, 화합물

HRID 913032노트

반응식

HRID 913032 반응식
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]=1[CH3:9].C(=O)([O-])[O-].[K+].[K+].[C:16]([CH:20](OC(F)(F)F)[OH:21])([F:19])([F:18])[F:17]>CO.C(OCC)(=O)C>[OH:1][C:2]1[C:7](=[O:8])[C:6]([CH:20]([OH:21])[C:16]([F:19])([F:18])[F:17])=[CH:5][NH:4][C:3]=1[CH3:9]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 3238144-Pyridinone,3-OH-2-MeHCID 57091037HCID 57091037, 화합물

생성물 1

HCID 25018649HCID 25018649, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-hydroxy-2-methyl-1H-pyridin-4-one (6.1 g, 48.7 mmol), potassium carbonate (17 g, 123 mmol), and CF3CH(OH)OCF3 (25 mL, 0.25 mol) was heated to reflux under a blanket of nitrogen for 30 h. The progress of the reaction was monitored by HPLC Method 1 (Example 24), which indicated 63% (peak percent area) of conversion to the product. The reaction mixture was diluted with methanol (50 mL), then filtered to remove solid particulates. The filtrate was evaporated to dryness to afford an oil. The oily residue was taken up in ethyl acetate (150 mL) and washed with a saturated ammonium chloride solution (80 mL). The organic fraction was collected and set aside. The pH of the aqueous fraction was adjusted to 6 with a dilute hydrochloric acid solution, and the resulting aqueous solution was extracted with ethyl acetate (2×40 mL). All the organic fractions were combined, then washed with saturated ammonium chloride, dried over Na2SO4, filtered and then evaporated to dryness to give an oil. On trituration with ether, 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one separated as a solid product and was collected by suction filtration (3.5 g, 33%). NMR data is described in Part C above.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under a blanket of nitrogen for 30 h
  3. filtrationfiltered
  4. customto remove solid particulates
  5. customThe filtrate was evaporated to dryness
  6. customto afford an oil
  7. washwashed with a saturated ammonium chloride solution (80 mL)
  8. customThe organic fraction was collected
  9. extractionthe resulting aqueous solution was extracted with ethyl acetate (2×40 mL)
  10. washwashed with saturated ammonium chloride
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customevaporated to dryness
  14. customto give an oil
  15. customOn trituration with ether, 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one separated as a solid product
  16. filtrationwas collected by suction filtration (3.5 g, 33%)

출처 및 근거

ORD 기록
ord-fa5bf6ff7de841329c2f426e6f13807b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026261B2

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