Potassium Carbonate → Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate

HRID 75965

반응식

HRID 75965 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:20]1[CH2:24][CH2:23][N:22]([CH3:25])[C:21]1=[O:26]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:20]2[CH2:24][CH2:23][N:22]([CH3:25])[C:21]2=[O:26])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 111829543-Bromo-1-methylpyrrolidin-2-one2회

생성물 1

HCID 66971906Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate수율 47.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of Methyl 3,5-dihydroxybenzoate (20 g) [CAS No. 2150-44-9] in dry DMF was added potassium carbonate (48 g) and the suspension stirred at ambient temperature under nitrogen. To this 3-Bromo-1-methyl-pyrrolidin-2-one (40 g) (Intermediate 5) [J. Med. Chem., 1987, 30, 1995-98] was added in three equal portions in 4 h intervals at room temperature and stirred overnight at ambient temperature. It was then quenched with water. The aqueous suspension was extracted with DCM. The to combined extracts were washed with water, brine, dried over Na2SO4, and filtered, concentrated under reduced pressure to get the thick liquid residue. The crude product was purified by column chromatography using silica gel as stationary phase and ethyl acetate: petroleum ether as a mobile phase to yield the product as white solid (15 g).

후처리

  1. stirringstirred overnight at ambient temperature
  2. customIt was then quenched with water
  3. extractionThe aqueous suspension was extracted with DCM
  4. washwere washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto get the thick liquid residue
  9. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-caf3ec1abbe14ca7aea8bc19a5ef8617
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835469B2

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