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

HRID 747214

Reaktionsgleichung

Reaktionsgleichung von HRID 747214
[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]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20788885Compound 3

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e1d1224ab8484c9da18ebb1ddba59775
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396847B2

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