Sodium Azide → (S)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-azidomethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

HRID 277828Notes

Reaction equation

HRID 277828 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([N:15]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30]OS(C4C=CC=C([N+]([O-])=O)C=4)(=O)=O)[O:27][C:26]3=[O:44])=[CH:21][C:20]=2[F:45])[CH2:16]1)([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]>CN(C=O)C>[C:5]([N:15]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@@H:28]([CH2:30][N:1]=[N+:2]=[N-:3])[O:27][C:26]3=[O:44])=[CH:21][C:20]=2[F:45])[CH2:16]1)([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54564258(R)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-[[(3-nitrophenylsulfonyl)oxy]methyl]-2-oxo-3-oxazolidinyl]phenyl]azetidine

Product 1

HCID 18684851(S)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-azidomethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium azide (1.44 g, 22.1 mmol) and (R)-(−)-N-carbobenzyloxy-3-[2-fluoro-4-[5-[[(3-nitrophenylsulfonyl)oxy]-methyl]-2-oxo-3-oxazolidinyl]phenyl]azetidine (Example 81, Step 6, 2.60 g, 4.44 mmol) in DMF (30 mL) was stirred for 16 hr, then filtered. The solvent was removed at 38°/0.75 mm and the residue extracted with ethyl acetate (100 mL) and washed with water (3×50 mL) and brine (50 mL). After drying over magnesium sulfate, filtration and evaporation gave a yellow oil. Chromatography over silica gel (150 g, 40-60 μm) eluting with 1-3% methanol-methylene chloride gave the title compound as a pale yellow foam. FAB-HRMS: theory 426.1577 (M+1); meas. 426.1580.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed at 38°/0.75 mm
  3. extractionthe residue extracted with ethyl acetate (100 mL)
  4. washwashed with water (3×50 mL) and brine (50 mL)
  5. dry with materialAfter drying over magnesium sulfate, filtration and evaporation
  6. customgave a yellow oil
  7. washChromatography over silica gel (150 g, 40-60 μm) eluting with 1-3% methanol-methylene chloride

Sources & evidence

ORD record
ord-a3fd387ac51a48b48ca5b68e3dee3d04
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

Loading…