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

HRID 474047ノート

反応式

HRID 474047 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6343Ethanethiol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cf45e1ca069644b79b8c0bfb394a79af
出典データセット
uspto-grants-2014_01
特許番号
US08637508B2

反応ノート

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