HCID 20616592, compound → HCID 20616634, compound

HRID 2119415Notes

Reaction equation

HRID 2119415 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3([C:20]4([CH3:25])[O:24][CH2:23][CH2:22][O:21]4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6]1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO.ClCCl>[NH2:1][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3([C:20]4([CH3:25])[O:21][CH2:22][CH2:23][O:24]4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6]1

Participants

5

Reactant 1

HCID 20616592HCID 20616592, compound

Product 1

HCID 20616634HCID 20616634, compound

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5(R)-azidomethyl-3-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]oxazolidin-2-one (1.46 g) and Lindlar catalyst (500 mg) in methanol (20 mL) and dichloromethane (4 mL) was hydrogenated at 1 atm for 2.5 hours at room temperature. After filtration of the catalyst, the filtrate was concentrated in vacuo to give 5(S)-aminomethyl-3-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]oxazolidin-2-one. To a solution of crude 5(S)-aminomethyl-3-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]oxazolidin-2-one thus obtained in dichloromethane (20 mL) was added triethylamine (1.2 mL) and acetic anhydride (0.8 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour, and then concentrated in vacuo. The residue was added acetic acid (30 mL) and water (3 mL), the resulting mixture was stirred at room temperature for 8 hours, and allowed to stand for overnight. After dilution with ethyl acetate, the mixture was washed with saturated sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, ethyl acetate:methanol=20:1) of the residue gave N-[5(S)-3-[4-(1-acetylcyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (800 mg).

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b855d94c03344240a1ac5bb6e94b51be
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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