Hydrochloric Acid → (S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-3,6-dihydro-2H-pyridin-4-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 428755Notes

Reaction equation

HRID 428755 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:14][CH2:15][N:16]([C:19](=[O:25])[CH2:20][O:21]C(=O)C)[CH2:17][CH:18]=3)=[C:9]([F:26])[CH:8]=2)[CH2:5][C@H:4]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:3]1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[OH:21][CH2:20][C:19]([N:16]1[CH2:17][CH:18]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([N:6]3[CH2:5][C@H:4]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:3][C:2]3=[O:1])=[CH:8][C:9]=2[F:26])[CH2:14][CH2:15]1)=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 18684835(S)-(-)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 9549076(S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-3,6-dihydro-2H-pyridin-4-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-(−)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 39, 475 mg) and anhydrous potassium carbonate (303 mg) in methanol (44 mL) is stirred under N2 at ambient temperature for 1.5 hours and then adjusted to pH 7 with aqueous hydrochloric acid (1M) and concentrated under reduced pressure. The residue is chromatographed on silica gel (230-400 mesh, 40 g), eluting with a gradient of methanol/chloroform (5/95-10/90), and those fractions with an Rf=0.21 by TLC (methanol/chloroform, 10/90) are pooled and concentrated under reduced pressure. The resulting foam is then triturated with methylene chloride/diethyl either and the precipitate filtered to give the title compound, Anal. calcd for C19H22N8O5F: C, 58.31;H, 5.67; N, 10.74. Found: C, 58.15; H, 5.64; N, 10.72.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is chromatographed on silica gel (230-400 mesh, 40 g)
  3. washeluting with a gradient of methanol/chloroform (5/95-10/90)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting foam is then triturated with methylene chloride/diethyl either
  6. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-06c734a87f5d4fe8b2a887cd1a689f75
Source dataset
uspto-grants-2001_11
Patent number
US06313307B1

Reaction notes

Loading…