Sodium Bicarbonate → HCID 21356563, compound

HRID 1167491Notes

Reaction equation

HRID 1167491 reaction equation
C(O[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:19]2[C:23]([CH3:24])=[CH:22][N:21]=[CH:20]2)=[C:16]([F:18])[CH:17]=1)=O)C1C=CC=CC=1.C([Li])CCC.[CH2:30]([O:34][C:35](=[O:39])CCC)[C@@H:31]1[O:33]C1.C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[F:18][C:16]1[CH:17]=[C:12]([N:11]2[CH2:9][C@H:30]([CH2:31][OH:33])[O:34][C:35]2=[O:39])[CH:13]=[CH:14][C:15]=1[N:19]1[C:23]([CH3:24])=[CH:22][N:21]=[CH:20]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 22996133HCID 22996133, compoundHCID 178418339Butyllithium

Product 1

HCID 21356563HCID 21356563, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyloxycarbonylamino-2-(5-methyl-imidazol-1-yl)fluorobenzene (3.2 g, 9.85 mmol) was dissolved in dry tetrahydrofuran (40 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 6.81 ml). After stirring for 20 minutes at −70°, (R)-glycidylbutyrate (1.57 g, 10.09 mmol) was added at −70°. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated MeOH (10 ml), stirred 15 minutes, then poured into aqueous sodium bicarbonate (5%, 100 ml) and extracted with EtOAc (3×40 ml). The combined extracts were washed with brine (20 ml), dried (magnesium sulfate) and evaporated. and the residue purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 5 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated, to give the desired product (0.86 g). MS (ESP): 292 (MH+) for C14H14FN3O3.

Workup

  1. temperaturecooled to −70°
  2. stirringStirring
  3. waitwas continued for 16 hours
  4. stirringstirred 15 minutes
  5. extractionextracted with EtOAc (3×40 ml)
  6. washThe combined extracts were washed with brine (20 ml)
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated
  9. customand the residue purified by chromatography on a 20 g silica Mega Bond Elut® column
  10. washeluting with
  11. temperaturea gradient increasing in polarity from 5 to 10% MeOH in dichloromethane
  12. customevaporated

Sources & evidence

ORD record
ord-0e7613a88e0f49ddac7c653588bd0d18
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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