Hydrochloric Acid → Trifluoro-methanesulfonic acid 2-hydroxy-3-(3-morpholin-4-yl-3-oxo-propionyl)-phenyl ester

HRID 1626716

반응식

HRID 1626716 반응식
[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C[O:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])[C:22]=1[OH:35].Cl>O1CCCC1.O>[OH:35][C:22]1[C:21]([C:20](=[O:19])[CH2:2][C:1]([N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)=[O:3])=[CH:26][CH:25]=[CH:24][C:23]=1[O:27][S:28]([C:31]([F:34])([F:32])[F:33])(=[O:30])=[O:29]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 155434-AcetylmorpholineHCID 2724682Lithium diisopropylamideHCID 11616395Methyl 2-hydroxy-3-(trifluoromethylsulfonyloxy)benzoate

생성물 1

HCID 11610960Trifluoro-methanesulfonic acid 2-hydroxy-3-(3-morpholin-4-yl-3-oxo-propionyl)-phenyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of N-acetylmorpholine (1.72 g, 13.3 mmol, 2 eq) in 30 ml dry tetrahydrofuran under nitrogen was cooled in an acetone/dry ice bath (−78° C.) and treated with LDA (10 ml, 2M solution in THF, 3 eq). The reaction mixture was stirred for 60 minutes then 2-hydroxy-3-trifluoromethanesulfonyloxy-benzoic acid methyl ester [α] (2 g, 6.6 mmol, 1 eq as a solution in 10 ml dry THF) was added. The reaction mixture was allowed to warm from −78° C. to room temperature and stirred over night. The reaction was diluted with water (4 ml) followed by 2M hydrochloric acid (40 ml), then extracted three times with dichloromethane. The extracts were combined, washed with brine, dried with magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography eluting with ethyl acetate to afford trifluoro-methanesulfonic acid 2-hydroxy-3-(3-morpholin-4-yl-3-oxo-propionyl)-phenyl ester [D]. Yield 1.06 g, 40%

후처리

  1. temperatureto warm from −78° C. to room temperature
  2. stirringstirred over night
  3. extractionextracted three times with dichloromethane
  4. washwashed with brine
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography
  9. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-a2acae143ffc4ae8b9c53dd95ce7d47c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785457B2

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