Oxazolo(4,5-b)pyridine → (S)-2-(tert-butoxycarbonyl)amino-1-(oxazolo[4,5-b]pyridin-2-yl)propan-1-ol

HRID 9926

Reaction equation

HRID 9926 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.C([Mg]Cl)(C)C.[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:26]C)[CH:24]=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([NH:22][CH:23]([CH3:26])[C@@H:24]([C:2]1[O:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2)[OH:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 10103159Oxazolo(4,5-b)pyridineHCID 10241556tert-butyl N-((2S)-1-oxobutan-2-yl)carbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 69617110(S)-2-(tert-butoxycarbonyl)amino-1-(oxazolo[4,5-b]pyridin-2-yl)propan-1-olYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a clean roundbottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in 30 mL THF and the reaction mixture was cooled to 0° C. under N2 atmosphere. Isopropylmagnesium chloride (2M in THF, 2.5 ml, 5 mmol ) was added. After stirring for 1 h at 0° C., (S)-2-(tert-butoxycarbonyl)aminobutyraldehyde (573 mg, 3 mmol) in 20 ml THF was added. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. After 2 h, the reaction mixture was quenched with saturated ammonium chloride solution and concentrated to dryness. The residue was extracted with EtOAc, then washed with brine, dried with anhyd. MgSO4, filtered and concentrated. The crude product was purified by chromatograph to yield 383 mg of the desired compound.

Workup

  1. customIn a clean roundbottom flask equipped
  2. stirringAfter stirring for 1 h at 0° C.
  3. customThe ice bath was removed
  4. temperatureto warm to room temperature
  5. customthe reaction mixture was quenched with saturated ammonium chloride solution
  6. concentrationconcentrated to dryness
  7. extractionThe residue was extracted with EtOAc
  8. washwashed with brine
  9. customdried with anhyd
  10. filtrationMgSO4, filtered
  11. concentrationconcentrated
  12. customThe crude product was purified by chromatograph

Sources & evidence

ORD record
ord-0f7f3745dfef454bbb9619689f26fde3
Source dataset
uspto-grants-2006_08
Patent number
US07091360B2

Linked notes

Loading…