Methyl formate → HCID 15276488, compound

HRID 1489452Notes

Reaction equation

HRID 1489452 reaction equation
C(OC)=O.[N-:5]=[N+:6]=[N-:7].[Na+].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C@H:17]1[O:23][C@H:18]1[C:19]([O:21][CH3:22])=[O:20].C(OCC)(=O)C>CO.O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C@H:17]([N:5]=[N+:6]=[N-:7])[C@@H:18]([OH:23])[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86751396HCID 86751396, compound

Product 1

HCID 15276488HCID 15276488, compoundYield 96.3%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
50 °C

Procedure

Under argon atmosphere, 1 ml of methyl formate and 360 mg of sodium azide were added to a solution of 237 mg of methyl (2R,3R)-3-(2,4-difluorophenyl)-2-epoxypropionate dissolved in 9 ml of methanol-water (8:1), and the mixture was stirred at 50° C. for 43 hours. After the reaction mixture was cooled, ethyl acetate and ice water were added to the reaction mixture, and the organic layer was collected by separation. After the organic layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=5:1) to obtain 274 mg of methyl (2R,3S)-3-(2,4-difluorophenyl)-3-azido-2-hydroxypropionate.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customthe organic layer was collected by separation
  3. washAfter the organic layer was washed with water
  4. customdried
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-190f76fd865c4c28ab84fbde524a5852
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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