Pyridine → (S)-N-[[3-[3-Fluro-4-[1-(carbobenzyloxy)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1637860Notes

Reaction equation

HRID 1637860 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].CN(C1C=CC=CN=1)C.[C:23]([N:33]1[CH2:36][CH:35]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][NH2:49])[O:45][C:44]3=[O:50])=[CH:39][C:38]=2[F:51])[CH2:34]1)([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl>[F:51][C:38]1[CH:39]=[C:40]([N:43]2[CH2:47][C@H:46]([CH2:48][NH:49][C:7](=[O:9])[CH3:8])[O:45][C:44]2=[O:50])[CH:41]=[CH:42][C:37]=1[CH:35]1[CH2:36][N:33]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:34]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 54291894(s)-(-)-Carbobenzyloxy-3-[2-fluoro-4-[5-aminomethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

Product 1

HCID 18393166(S)-N-[[3-[3-Fluro-4-[1-(carbobenzyloxy)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.0 mL), acetic anhydride (1.0 mL) and a few crystals of 4 dimethylaminopyridine were added to a stirred solution of (S)-(-)-N-carbobenzyloxy-3-[2-fluoro-4-[5-aminomethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine (Example 81, Step 8, 1.42 g, 3.56 mmol) in methylene chloride (30 mL), then stirred for 1 hr. The solvents were removed at 38°/0.75 mm and the residue chromatographed over silica gel (50 g, 40-60 μm) eluting with 1-2% methanol-chloroform. The title compound was isolated as a white foam. FAB-HRMS: theory 442.1778 (M+1); meas. 442.1777.

Workup

  1. customThe solvents were removed at 38°/0.75 mm
  2. customthe residue chromatographed over silica gel (50 g, 40-60 μm)
  3. washeluting with 1-2% methanol-chloroform

Sources & evidence

ORD record
ord-4bdb0d80917d41058dedee59378ff281
Source dataset
uspto-grants-2000_03
Patent number
US06043266

Reaction notes

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