Benzaldehyde → HCID 69085967, compound

HRID 2362447Notes

Reaction equation

HRID 2362447 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]1([C:19]#[C:20][C:21]2[CH:22]=[C:23]([CH2:27][C:28]([OH:30])=[O:29])[CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1>[OH:38][C@@H:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]#[C:19][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:22]=1)[C:28]([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 7912DiisopropylamineHCID 69085566HCID 69085566, compoundHCID 178418339Butyllithium

Product 1

HCID 69085967HCID 69085967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To diisopropylamine (0.241 mL, 1.693 mmol) in tetrahydrofuran (10 mL) under nitrogen at −78° C. was added n-BuLi (0.677 mL, 1.693 mmol). After 60 min, the colorless solution was warmed to −20° C. and a solution of 2-(3-(phenylethynyl)phenyl)acetic acid (200 mg, 0.847 mmol; Araldi, G. L.; Liao, Y.; Brugger, N. Hydrazide Deriviatives as Prostaglandin Receptor Modulators. WO 2005/012232 A2, 2005) in tetrahydrofuran (5 mL) was added resulting in a red solution which was allowed to stir for 45 min as the cooling bath temperature rose to 5° C. The reaction was recooled to −30° C., benzaldehyde (0.103 mL, 1.016 mmol) was added dropwise resulting in immediate disappearance of the red color and the cooling bath was removed. After 48 h, the reaction mixture was quenched with 1N HCl (20 mL), extracted with ethyl acetate (3×20 mL), washed with brine, dried over MgSO4, filtered and concentrated providing (2S,3R)-3-hydroxy-3-phenyl-2-(3-(phenylethynyl)phenyl)propanoic acid as an amber oil which was used in the next step without further purification or characterization.

Workup

  1. customresulting in a red solution which
  2. customrose to 5° C
  3. customwas recooled to −30° C.
  4. customresulting in immediate disappearance of the red color
  5. customthe cooling bath was removed
  6. waitAfter 48 h
  7. customthe reaction mixture was quenched with 1N HCl (20 mL)
  8. extractionextracted with ethyl acetate (3×20 mL)
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-d7fd9ed06950417e8a5ffd59651447b2
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

Loading…