Boron trifluoride etherate → N-[1-(6-Bromo-pyridin-2-yl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

HRID 538306노트

반응식

HRID 538306 반응식
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:19][C:20](=[O:23])[CH2:21][Cl:22])([CH2:14][O:15]COC)[CH2:9][O:10]COC)[CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>C(S)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:19][C:20](=[O:23])[CH2:21][Cl:22])([CH2:14][OH:15])[CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 8000Boron trifluoride etherateHCID 86668020N-[1-(6-Bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethyl]-2-chloro-acetamide

생성물 1

HCID 86668021N-[1-(6-Bromo-pyridin-2-yl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

시약·촉매·용매 1

HCID 6343Ethanethiol용매

실험 절차

To a solution of N-[1-(6-bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethyl]-2-chloro-acetamide (9.0 g, 21.861 mmol) in ethanethiol (30 ml) and BF3.Et2O (9.3 g, 141.93 mmol) was added at 0° C. and stirred for 10 min. Stirring was continued for 3 h at rt. Reaction mixture was quenched with saturated NaHCO3 solution and the product formed was extracted with ethyl acetate. Organic layer was separated and washed with brine solution, followed by drying over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure and purified by column chromatography using 2% methanol in chloroform to obtain title compound as a brown liquid. Yield=5.5 g (77%). TLC (10% methanol in chloroform) Rf=0.51; LCMS: RtH8=0.916, [M+1]=322.9 and 324.8; HPLC RtH9=5.931 min (89%); 1H NMR (400 MHz, CDCl3): δ 8.27 (s, 1H), 7.56 (t, 1H), 7.42-7.39 (m, 2H), 4.38 (s, 2H), 4.09-4.07 (m, 4H), 3.95 (d, 2H).

후처리

  1. stirringStirring
  2. waitwas continued for 3 h at rt
  3. customReaction mixture
  4. customwas quenched with saturated NaHCO3 solution
  5. customthe product formed
  6. extractionwas extracted with ethyl acetate
  7. customOrganic layer was separated
  8. washwashed with brine solution
  9. dry with materialby drying over anhydrous Na2SO4
  10. concentrationOrganic layer was concentrated under reduced pressure
  11. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-3005d89d72e94b4090b685e9090052da
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865712B2

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