HCID 20616629, compound → HCID 20616635, compound

HRID 2119413Notes

Reaction equation

HRID 2119413 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]#[N:21])[CH2:19][CH2:18]3)=[C:13]([F:22])[CH:12]=2)[CH2:6]1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[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]#[N:21])[CH2:18][CH2:19]3)=[C:13]([F:22])[CH:12]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 20616629HCID 20616629, compound

Product 1

HCID 20616635HCID 20616635, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5(R)-azidomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one (122 mg) and Lindlar catalyst (12 mg) in methanol (5 mL) was hydrogenated at 1 atm for 3 hours at room temperature. After filtration of the catalyst, the filtrate was concentrated in vacuo to give 5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one. To a solution of crude 5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one thus obtained in dichloromethane (2 mL) was added pyridine (96 mg) and methanesulfonyl chloride (70 mg) at 0° C., and the mixture was stirred at the same temperature for 30 min. The mixture was washed with water and 5% hydrochloric acid, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, ethyl acetate) of the residue gave N-[5(S)-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]-2-oxooxazolidin-5-ylmethyl]methanesulfonylamide. MS (EI+) m/z: 353 (M+).

Workup

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

Sources & evidence

ORD record
ord-898ebe9eb13f47f2a0abfc0a0a4f680e
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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