Pyridine → HCID 18684834, compound

HRID 1004813Notes

Reaction equation

HRID 1004813 reaction equation
CC([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH2:26])[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=[O:7])(C)C.N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[C:35]([NH:26][CH2:25][C@@H:23]1[O:22][C:21](=[O:27])[N:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([OH:5])=[O:7])[CH2:13][CH2:12]3)=[C:15]([F:28])[CH:16]=2)[CH2:24]1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54424107HCID 54424107, compound

Product 1

HCID 18684834HCID 18684834, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-(-)-4-[4-[5-(aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 8, 9.45 g) in dry methylene chloride (96 mL) under N2 is treated with pyridine (5.82 mL) and acetic anhydride (3.40 mL), and the resulting mixture is stirred at ambient temperature for four hours, diluted with methylene chloride (25 mL), washed with water (25 mL), saturated aqueous sodium bicarbonate (25 mL) and saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is then chromatographed on silica gel (230-400 mesh, 350 g), eluting with a gradient of methanol/chloroform (2.5/97.5-7.5/92.5). Pooling and concentration of those fractions with an Rf =0.51 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 144-146° C.

Workup

  1. washwashed with water (25 mL), saturated aqueous sodium bicarbonate (25 mL) and saline (25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude product which
  5. customis then chromatographed on silica gel (230-400 mesh, 350 g)
  6. washeluting with a gradient of methanol/chloroform (2.5/97.5-7.5/92.5)

Sources & evidence

ORD record
ord-04979973ffee452d86c9e54343fbacc7
Source dataset
uspto-grants-2000_04
Patent number
US06051716

Reaction notes

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