Water → HCID 86677499, compound

HRID 1400654Notes

Reaction equation

HRID 1400654 reaction equation
[CH3:1][C:2]1([CH3:24])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([CH2:14]OS(C)(=O)=O)[C@@H:4]([C:20]([O:22][CH3:23])=[O:21])[O:3]1.[N-:25]=[N+:26]=[N-:27].[Na+].O>CN(C=O)C>[N:25]([CH2:14][C@@H:5]1[C@@H:4]([C:20]([O:22][CH3:23])=[O:21])[O:3][C:2]([CH3:24])([CH3:1])[N:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86677500HCID 86677500, compound

Product 1

HCID 86677499HCID 86677499, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Compound XXXVII (0.30 g, 0.80 mmol) was dissolved in DMF (10 mL) followed by the addition of NBu4Br (0.092 g, 0.28 mmol) and then NaN3 (0.15 g, 2.32 mmol). The mixture was heated at 70° C. for 7 h. Water (30 mL) was added to the cooled reaction mixture and it was extracted with EtOAc (3×20 mL). The organic phase was separated, dried over Na2SO4 and evaporated. The residue was purified on a silica gel column (3:1 hexane/EtOAc→1:1 hexane/EtOAc) to yield (4R,5S)-3-tert-butyl 5-methyl 4-(azidomethyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate XXXVIII (0.078 g, 0.25 mmol, 31%). ESIMS found for C13H22N4O5 m/z 337 (M+Na).

Workup

  1. additionfollowed by the addition of NBu4Br (0.092 g, 0.28 mmol)
  2. extractionwas extracted with EtOAc (3×20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified on a silica gel column (3:1 hexane/EtOAc→1:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-ac835bee100a47acb96addb01c40530b
Source dataset
uspto-grants-2014_12
Patent number
US08906868B2

Reaction notes

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