Imidazole → HCID 15286443, compound

HRID 1175453Notes

Reaction equation

HRID 1175453 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH3:7][C:8]([Si:11](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:10])[CH3:9].N1C=CN=C1>CN(C=O)C>[Si:11]([O:1][C@H:2]([CH3:6])[C:3]([OH:5])=[O:4])([C:8]([CH3:10])([CH3:9])[CH3:7])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 61503D-Lactic AcidHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 15286443HCID 15286443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-2-hydroxypropanoic acid (5 g) in DMF (20 ml) was added TBDPSCl (33.0 g) and imidazole (16.4 g). The reaction was then stirred overnight at RT. The reaction was partitioned between EtOAc (200 ml) and H2O (200 ml). The organics were recovered and washed with 10% citric acid (200 ml), H2O (200 ml) and finally brine (200 ml). The organics were then collected, dried (MgSO4) before being reduced in vacuo. The residue was dissolved in MeOH (200 ml), cooled in an ice bath and potassium carbonate (6.9 g) in H2O was added. After stirring at room temperature for 6 h the solvent was removed in vacuo and the residue diluted with H2O (100 ml). The pH was then adjusted to pH 4 with 10% citric acid, and the aqueous extracted three times with EtOAc (3×200 ml). The organics were collected dried MgSO4 before reducing in vacuo to give the subtitle compound as a colourless oil. Yield: 7.5 g

Workup

  1. customThe reaction was partitioned between EtOAc (200 ml) and H2O (200 ml)
  2. customThe organics were recovered
  3. washwashed with 10% citric acid (200 ml), H2O (200 ml) and finally brine (200 ml)
  4. customThe organics were then collected
  5. dry with materialdried (MgSO4)
  6. dissolutionThe residue was dissolved in MeOH (200 ml)
  7. temperaturecooled in an ice bath
  8. additionpotassium carbonate (6.9 g) in H2O was added
  9. stirringAfter stirring at room temperature for 6 h the solvent
  10. customwas removed in vacuo
  11. additionthe residue diluted with H2O (100 ml)
  12. extractionthe aqueous extracted three times with EtOAc (3×200 ml)
  13. customThe organics were collected dried MgSO4

Sources & evidence

ORD record
ord-a05c7385c1f5441280ba227a7e9a958e
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

Loading…