Sodium Azide → HCID 86621904, compound

HRID 734193Notes

Reaction equation

HRID 734193 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:16][CH:15]([CH2:17]I)[O:14][C:13]2=[O:19])[CH:9]=[CH:8][C:7]=1[N:20]1[CH2:28][CH:27]2[CH:22]([O:23][CH2:24][CH2:25][N:26]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:21]1>CN(C)C=O>[N:1]([CH2:17][CH:15]1[O:14][C:13](=[O:19])[N:12]([C:10]2[CH:9]=[CH:8][C:7]([N:20]3[CH2:28][CH:27]4[CH:22]([O:23][CH2:24][CH2:25][N:26]4[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:21]3)=[C:6]([F:5])[CH:11]=2)[CH2:16]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11955886HCID 11955886, compound

Product 1

HCID 86621904HCID 86621904, compoundYield 124.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (1.21 g) was added to the compound tertbutyl 6-{2-fluoro-4-[5-(iodomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}hexahydropyrrolo[3,4-b][1,4]oxazine-4(4aH)-carboxylate (2 g) obtained from example 02 above in dimethyl formamide (30 mL) and the reaction mixture was stirred at 60° C. for 3 hrs. The reaction mixture was filtered and the filtrate was concentrated to give the title compound (2.1 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6003709255574dd4807789589968adc7
Source dataset
uspto-grants-2009_09
Patent number
US07592335B2

Reaction notes

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