Methyl chloroformate → (S)-N-[[3-[3-Fluoro-4-[1-(carboxymethyl)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 428779Notes

Reaction equation

HRID 428779 reaction equation
[CH2:1](N(CC)CC)C.Cl[C:9]([O:11]C)=[O:10].[F:13][C:14]1[CH:15]=[C:16]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:17]=[CH:18][C:19]=1[CH:20]1[CH2:23][NH:22][CH2:21]1>C(Cl)(Cl)Cl>[F:13][C:14]1[CH:15]=[C:16]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:17]=[CH:18][C:19]=1[CH:20]1[CH2:23][N:22]([CH2:1][C:9]([OH:11])=[O:10])[CH2:21]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 53667482(S)-N-[[3-[3-Fluoro-4-[3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 54000610(S)-N-[[3-[3-Fluoro-4-[1-(carboxymethyl)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (150 μL, 1.08 mmol) and methyl chloroformate (65 μL, 0.84 mmol) were added to a chloroform (5 mL) suspension of (S)-N-[[3-[3-fluoro-4-[3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 82, 153 mg, 0.50 mmol) and stirred overnight. Additional chloroform (25 mL) was added and the solution washed with water (15 mL) and brine (15 mL). Drying over magnesium sulfate, filtration, and evaporation gave a foam. Chromatography over silica gel (50 g, 40-60 μm) eluting with 1-3% methanol-chloroform gave the title compound as a white solid. FAB-HRMS: theory 366.1465 (M+1); meas. 366.1468.

Workup

  1. washthe solution washed with water (15 mL) and brine (15 mL)
  2. dry with materialDrying over magnesium sulfate, filtration, and evaporation
  3. customgave a foam
  4. washChromatography over silica gel (50 g, 40-60 μm) eluting with 1-3% methanol-chloroform

Sources & evidence

ORD record
ord-c51c498c4d3043bc8a00fecf3c6a1c1c
Source dataset
uspto-grants-2001_11
Patent number
US06313307B1

Reaction notes

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