Hydrochloric Acid → HCID 15887509, compound

HRID 277818Notes

Reaction equation

HRID 277818 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:14][N:15]([C:19](=[O:25])[CH2:20][O:21]C(=O)C)[CH2:16][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.O.C(Cl)Cl>[OH:21][CH2:20][C:19]([N:15]1[CH2:16][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]1)=[O:25]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15887508HCID 15887508, compound

Product 1

HCID 15887509HCID 15887509, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-5,6-dihydro-2H-pyridin-3-yl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 70, Step 3, 105 mg) and anhydrous potassium carbonate (67 mg) in methanol (4.8 mL) is stirred under N2 at ambient temperature for 2 hrs and is then neutralized with hydrochloric acid (1 M), diluted with water (10 mL) and methylene chloride (40 mL), and the layers are separated. The organic phase is washed with saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which is then chromatographed on silica gel (70-230 mesh, 15 g), eluting with methanol/methylene chloride (5/95). Pooling and concentration of those fractions with an Rf=0.30 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 188-190° C.

Workup

  1. customthe layers are separated
  2. washThe organic phase is washed with saline (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product, which
  6. customis then chromatographed on silica gel (70-230 mesh, 15 g)
  7. washeluting with methanol/methylene chloride (5/95)

Sources & evidence

ORD record
ord-558edd7102e34ae6be19b139baffc134
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

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