Methyl formate → HCID 15549884, compound

HRID 975276Notes

Reaction equation

HRID 975276 reaction equation
[CH:1]1([C@H:4]2[O:10][C@H:5]2[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.C(OC)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>CO.O>[CH:1]1([C@H:4]([N:15]=[N+:16]=[N-:17])[C@@H:5]([OH:10])[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 33557Sodium AzideHCID 15549883HCID 15549883, compound

Product 1

HCID 15549884HCID 15549884, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.89 g of methyl (2R,3R)-3-cyclopropyl-2,3-epoxypropionate in 112.5 ml of methanol-water (8:1) are added 14 ml of methyl formate and 16.60 g of sodium azide. Then, the reaction mixture is stirred at 50° C. overnight. The reaction mixture is cooled to room temperature and evaporated to remove methanol. The residue is dissolved in ethyl acetate. The solution is washed with brine and dried. The solvent is removed in vacuo. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 2.61 g of methyl (2R,3S)-3-cyclopropyl-3-azido-2-hydroxypropionate.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customevaporated
  3. customto remove methanol
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washThe solution is washed with brine
  6. customdried
  7. customThe solvent is removed in vacuo
  8. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0970ef93ba534d75b031e2fff9e6de52
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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