Potassium Hydroxide → HCID 86677501, compound

HRID 1400655Notes

Reaction equation

HRID 1400655 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@@H:9]([C:10]([O:12]C)=[O:11])[O:8][C:7]([CH3:15])([CH3:14])[N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+:2]=[N-:3].[OH-].[K+]>CO>[N:1]([CH2:4][C@@H:5]1[C@@H:9]([C:10]([OH:12])=[O:11])[O:8][C:7]([CH3:15])([CH3:14])[N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86677499HCID 86677499, compound

Product 1

HCID 86677501HCID 86677501, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound XXXVIII (0.064 g, 0.21 mmol) was dissolved in MeOH (1 mL) and a solution of 2M KOH (0.15 mL, 0.3 mmol) was added. The solution was stirred for 2 h at room temperature. The solvent was evaporated under reduced pressure and the resulting residue was treated with water and extracted with diethyl ether. The aqueous phase was separated, acidified with 1N HCl (pH=2) and extracted with EtOAc (3×15 mL). The organic phase was dried over Na2SO4 and evaporated producing (4R,5S)-4-(azidomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-5-carboxylic acid XXXIX (0.057 g, 0.19 mmol, 92%). ESIMS found for C12H20N4O5 m/z 301 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe resulting residue was treated with water
  3. extractionextracted with diethyl ether
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc (3×15 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-c4ba52f8f2704e4a99be279ac04eb60e
Source dataset
uspto-grants-2014_12
Patent number
US08906868B2

Reaction notes

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