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

HRID 428777Notes

Reaction equation

HRID 428777 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[C:14]([N:24]1[CH2:27][CH:26]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:38][C@H:37]([CH2:39][NH2:40])[O:36][C:35]3=[O:41])=[CH:30][C:29]=2[F:42])[CH2:25]1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:42][C:29]1[CH:30]=[C:31]([N:34]2[CH2:38][C@H:37]([CH2:39][NH:40][C:7](=[O:9])[CH3:8])[O:36][C:35]2=[O:41])[CH:32]=[CH:33][C:28]=1[CH:26]1[CH2:27][N:24]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:25]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 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 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-30c3f7ec868743ad930d3b739de72cd1
Source dataset
uspto-grants-2001_11
Patent number
US06313307B1

Reaction notes

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