HCID 76694870, compound → HCID 68469176, compound

HRID 1867254Notes

Reaction equation

HRID 1867254 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]3[CH:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:12]([CH:14]=[O:15])=[N:13][N:7]3[C:6]=2[CH:22]=1.[CH2:23]([Mg]Cl)[CH3:24]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]3[CH:11]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:12]([CH:14]([OH:15])[CH2:23][CH3:24])=[N:13][N:7]3[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 76694870HCID 76694870, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 68469176HCID 68469176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of racemic aldehyde (2-1) (0.03 g, 0.1 mmol) in THF (6 mL) at −78° C. was treated with a solution of ethylmagnesium chloride (0.05 mL of a 2M soln in THF). A heavy precipitate formed immediately. The reaction was quenched with water and the mixture extracted with EtOAc. The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was dissolved in MeCN (0.5 mL) and purified by reverse phase HPLC (YMC J-sphere H80 20×50 mm; eluted with 5-95% MeCN/water+0.1% TFA) to provide (2-2) as a mixture (˜2:1) of isomers. LRMS nm/z (M+H) 327.2 found, 327.2 required.

Workup

  1. customA heavy precipitate formed immediately
  2. customThe reaction was quenched with water
  3. extractionthe mixture extracted with EtOAc
  4. washThe organic solution was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in MeCN (0.5 mL)
  9. custompurified by reverse phase HPLC (YMC J-sphere H80 20×50 mm; eluted with 5-95% MeCN/water+0.1% TFA)

Sources & evidence

ORD record
ord-8eabf49ba7d44ff2af08da52328ed7c3
Source dataset
uspto-grants-2009_12
Patent number
US07632833B2

Reaction notes

Loading…