4-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidine → 4-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid {3-[2-methyl-4-(2-nitro-phenyl)-piperazin-1-yl)-propyl)-amide

HRID 1275204Notes

Reaction equation

HRID 1275204 reaction equation
[CH3:1][C@@H:2]1[N:7]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][CH2:5][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:3]1.[N+](C1C=CC([O:30][C:31]([N:33]2[CH:37]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=3)[CH2:36][O:35][C:34]2=[O:46])=O)=CC=1)([O-])=O>C1COCC1>[CH3:1][CH:2]1[CH2:3][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][NH:11][C:31]([N:33]1[CH:37]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=2)[CH2:36][O:35][C:34]1=[O:46])=[O:30]

Participants

4

Reactant 2

HCID 220490874-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidineHCID 54236944(S)-(+)-3-methyl-1-(2-nitrophenyl)-4-(3-aminopropyl)-piperazine

Product 1

HCID 213573924-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid {3-[2-methyl-4-(2-nitro-phenyl)-piperazin-1-yl)-propyl)-amideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(+)-3-methyl-1-(2-nitrophenyl)-4-(3-aminopropyl)-piperazine (35 mg, 0.126 mmol) in 10 mL of THF, 4-(3,4-difluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester (50 mg, 0.137 mmol) was added and the resulting yellow solution was stirred under argon atmosphere for 2 h at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc followed by MeOH:EtOAc=1:9 (Rf =0.58, MeOH:EtOAc=1:3) to obtain 4-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid {3-[2-methyl-4-(2-nitro-phenyl)-piperazin-1-yl)-propyl}-amide (55 mg, 87%) The compound was dissolved in CH2Cl2 (3 mL) and was treated with 1N HCl in ether (1 mL). The solvent was removed in vacuo to give the corresponding hydrochloride salt as a pale yellow solid. M. P. 115-119° C.; [α]D =+38.3, (c=0.22, CH2Cl2); Anal. Calcd. For C24H28N5O5F2Cl.0.72 C6H12 : C, 56.50; H, 6.38; N, 11.63. Found: C, 56.63; H, 6.35; N, 10.08.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-02aafea708c245a7844833fec09e7a61
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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