Ethyl Acetate → (S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

HRID 428747Notes

Reaction equation

HRID 428747 reaction equation
CC(OC([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]OS(C)(=O)=O)[O:22][C:21]3=[O:31])=[CH:16][C:15]=2[F:32])[CH2:10][CH2:9]1)=O)(C)C.[N-:33]=[N+]=[N-].[Na+].[C:37]([O:40]CC)(=O)[CH3:38]>CN(C)C=O>[O:31]=[C:21]1[N:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[C:15]([F:32])[CH:16]=2)[CH2:24][C@H:23]([CH2:25][NH:33][C:37](=[O:40])[CH3:38])[O:22]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 54118607HCID 54118607, compound

Product 1

HCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-(-)-4-[4-[5-[[(methylsulfonyl)oxy]methyl]-2-oxo-3-oxazolidinyl]-2- fluorophenyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 6, 13.83 g) and sodium azide (7.62 g) in dry dimethylformamide (117 mL) under N2 is stirred at 60° C. for five hours and at ambient temperature for 16 hours. The mixture is then diluted with ethyl acetate (200 mL), washed with water (8×100 mL) and saline (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound, mp 109-110° C.

Workup

  1. washwashed with water (8×100 mL) and saline (100 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2ee78eb360f4ce9b0a63e2764ed4a22
Source dataset
uspto-grants-2001_11
Patent number
US06313307B1

Reaction notes

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