Imidazole → HCID 57504575, compound

HRID 1098083Notes

Reaction equation

HRID 1098083 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH3:14][N:15]([CH3:25])[CH2:16][CH2:17][C@H:18]([OH:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>CN(C=O)C.CCOC(C)=O>[Si:10]([O:24][C@@H:18]([CH2:17][CH2:16][N:15]([CH3:25])[CH3:14])[C:19]([O:21][CH2:22][CH3:23])=[O:20])([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 57438627HCID 57438627, compound

Product 1

HCID 57504575HCID 57504575, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (1.98 g, 29.10 mmol) and TBDMSCl (2.34 g, 15.52 mmol) was added to a stirred solution of ethyl (2S)-4-(dimethylamino)-2-hydroxybutanoate (Step 1) (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and EtOAc were added and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed three times with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with heptane/EtOAc:2/1) to give the title compound as a colourless oil (2.73 g), 1H NMR (300 MHz, DMSO) δ 4.28 (m, 1H), 4.18 (m, 2H), 2.44 (m, 1H), 2.30 (m, 1H), 2.22 (s, 6H), 1.87 (m, 2H), 1.28 (t, 3H), 0.90 (s, 9H), 0.08 (d, 6H).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washwashed three times with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with column chromatography (silica gel, eluting with heptane/EtOAc:2/1)

Sources & evidence

ORD record
ord-9aa5c163cf5a44c1b79b7629a882c17c
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…