Imidazole → HCID 10016539, compound

HRID 18842Notes

Reaction equation

HRID 18842 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1.CCOCC>[CH3:12][O:11][C:1](=[O:10])[CH:2]([O:3][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 10016539HCID 10016539, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available methyl (S)-mandelate (2.39 g, 14.4 mmol) in dichloromethane (50 mL) is added imidazole (1.18 g, 17.3 mmol), tert-butyldimethylsilyl chloride (2.38 g, 15.8 mmol) and 4-dimethylaminopyridine (176 mg, 1.44 mmol). The mixture is stirred for 16 hrs then diluted with ether, washed with water, brine, then dried (MgSO4), filtered and concentrated. The residue is purified by chromatography on silica gel; elution with EtOAc:heptane (25:75) gives 3.67 g of the product. 1H NMR (CDCl3) δ 7.45-7.40 (m, 2 H), 7.35-7.25 (m, 3 H), 5.20 (s, 1 H), 3.65 (s, 3 H), 0.90 (s, 9 H), 0.10 (s, 3 H), 0.05 (s, 3 H); MS: m/z 281 (M++1)

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on silica gel
  6. washelution with EtOAc:heptane (25:75)

Sources & evidence

ORD record
ord-b0ff3415eb9e4d9a87f052cf71da7550
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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