2,2-Difluoro-2-(fluorosulfonyl)acetic acid → Methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoate

HRID 2241939노트

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HRID 2241939 반응식
[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:26])[CH2:24][OH:25])[CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[N:9][CH:10]=1)=[O:4].[F:28][C:29]([F:37])(S(F)(=O)=O)C(O)=O>C(#N)C.[Cu]I>[F:28][CH:29]([F:37])[O:25][CH2:24][C@@H:23]([O:22][C:20]1[CH:19]=[C:14]([CH:13]=[C:12]([O:11][C:8]2[CH:7]=[N:6][C:5]([C:3](=[O:4])[N:2]([CH3:1])[CH3:27])=[CH:10][N:9]=2)[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:26]

참가 물질

5

반응물 2

HCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 59205095methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(2S)-1-hydroxypropan-2-yl]oxy-benzoate

생성물 1

HCID 59205092Methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매2회

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온도
55 °C

실험 절차

A solution of methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(2S)-1-hydroxypropan-2-yl]oxy-benzoate (94 g, 250 mmol) in acetonitrile (1130 mL) was degassed with nitrogen then copper(I) iodide (9.54 g, 50 mmol) was charged and the solution was heated to 55° C. A solution of 2,2-difluoro-2-fluorosulfonyl-acetic acid (CAS no. 1717-59-5) (46.6 mL, 450 mmol) in acetonitrile (188 mL) was charged dropwise. After 3 hours the solvent was evaporated under reduced pressure at 25° C. The residue was taken up in dichloromethane (500 mL) and filtered. The solid was washed further with dichloromethane until the washings were clear. The solvent was evaporated under reduced pressure at 25° C. and the residue was purified by flash chromatography eluting with 100% ethyl acetate to afford the title compound (54 g).

후처리

  1. customAfter 3 hours the solvent was evaporated under reduced pressure at 25° C
  2. filtrationfiltered
  3. washThe solid was washed further with dichloromethane until the washings
  4. customThe solvent was evaporated under reduced pressure at 25° C.
  5. customthe residue was purified by flash chromatography
  6. washeluting with 100% ethyl acetate

출처 및 근거

ORD 기록
ord-a0976f0a22e74f5ab388bc11dff670c0
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671060B2

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