Imidazole → HCID 10540806, compound

HRID 751662Notes

Reaction equation

HRID 751662 reaction equation
[NH2:1][C@@H:2]([CH2:11][OH:12])[C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C@@H:2]([CH2:11][O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C@H:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:4]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diol

Product 1

HCID 10540806HCID 10540806, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (1S,2S)-2-amino-1-phenyl-1,3-propanediol (2.07 g, 12.4 mmol) in DMF (10 mL) was added imidazole (1.0 g, 14.7 mmol) and tert-butyldimethylsilyl chloride (2.30 g, 15.3 mmol). After stirring at rt for 12 h the mixture was added to diluted brine (150 mL, water/brine:1/1). Extraction with ethyl acetate (4×30 mL), washing of the combined extracts with brine (30 mL) and drying (MgSO4) gave after concentration a residue which was purified by flash chromatography on silica gel (eluent: ethyl acetate). The title compound was obtained as colourless oil. δH (CDCl3): 0.24, 0.26 (6H, 2s), 1.12 (9H, s), 2.50–2.78 (3H, br s), 3.16 (1H, ddd), 3.78 (1H, dd), 3.85 (1H, dd), 4.84 (1H, d), 7.49–7.55 (5H, m); m/z (ES+)=282.32 [M+H]+; RT=2.87 min.

Workup

  1. extractionExtraction with ethyl acetate (4×30 mL)
  2. washwashing of the combined extracts with brine (30 mL)
  3. dry with materialdrying (MgSO4)
  4. customgave
  5. concentrationafter concentration a residue which
  6. customwas purified by flash chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-1ba61880048b4b2a96465674fa1e7ec0
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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