Dimethylformamide → (5S)-5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one

HRID 2066814Notes

Reaction equation

HRID 2066814 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]Cl)[O:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[N-:21]=[N+:22]=[N-:23].[Na+]>ClCCl.CO>[N:21]([CH2:13][C@H:11]1[O:10][C:9](=[O:15])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 14698771HCID 14698771, compound2×

Product 1

HCID 59409879(5S)-5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
120 °C

Procedure

A 40 ml vial was charged with 3-benzyl-5-(chloromethyl)-1,3-oxazolidin-2-one (112 mg, 0.5 mmol, INTERMEDIATE 13), dimethylformamide (5 ml), and sodium azide (130 mg, 2 mmol). The mixture was heated to 120° C. for 15 h. The crude was applied to a pad of silica and washed with methanol (2×10 ml). The organics were pooled and concentrated to provide a residue. The title compound was isolated on silica gel eluting with a gradient of dichloromethane/methanol from 0% to 100% to provide 100 mg (86%) as a tan oil. Mass spectrum (ESI) 233.2 (M+1).

Workup

  1. washwashed with methanol (2×10 ml)
  2. concentrationconcentrated
  3. customto provide a residue

Sources & evidence

ORD record
ord-25be5566f08c44b6ab49198142c9811f
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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