Triethylamine → Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

HRID 747214

반응식

HRID 747214 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1[I:8].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1[I:8]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20788885Compound 3

생성물 1

HCID 23624705Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(hydroxymethyl)oxazolidin-2-one (6.07 g, 18 mM) in dry dichloromethane (200 ml) under nitrogen was treated with triethylamine (2.54 g, 25 mM), and methanesulfonyl chloride (2.47 g, 22 mM) run in dropwise over 30 minutes at 0°. After stirring 2 hours at 0°, the mixture was diluted with water (200 ml), the organic layer separated, washed with hydrochloric acid (2N, 100 ml), sodium bicarbonate solution (5%, 100 ml), brine (100 ml) and dried (magnesium sulfate). The residue after evaporation was dissolved in the minimum of dichloromethane, and excess isohexane added to precipitate the desired product (7.05 g).

후처리

  1. customdropwise over 30 minutes
  2. customat 0°
  3. customthe organic layer separated
  4. washwashed with hydrochloric acid (2N, 100 ml), sodium bicarbonate solution (5%, 100 ml), brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customThe residue after evaporation
  7. dissolutionwas dissolved in the minimum of dichloromethane, and excess isohexane
  8. additionadded
  9. customto precipitate the desired product (7.05 g)

출처 및 근거

ORD 기록
ord-e1d1224ab8484c9da18ebb1ddba59775
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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