Imidazole → HCID 11210526, compound

HRID 1867596Notes

Reaction equation

HRID 1867596 reaction equation
N1C=CN=C1.[C:6]([Si:10]([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)Cl)([CH3:9])([CH3:8])[CH3:7].Cl.[CH3:25][O:26][C:27](=[O:32])[CH:28]([CH2:30][OH:31])[NH2:29]>CN(C)C=O>[Si:10]([O:31][CH2:30][C@@H:28]([C:27]([O:26][CH3:25])=[O:32])[NH2:29])([C:6]([CH3:9])([CH3:8])[CH3:7])([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

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 517373Methyl DL-serinate hydrochloride

Product 1

HCID 11210526HCID 11210526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.82 g, 41.43 mmol) and tert-butyldiphenylchlorosilane (3.23 mL, 12.43 mmol) was added to a solution of DL-serine methyl ester hydrochloride (1.41 g, 11.84 mmol) in dimethylformamide (6 mL). After 16 h, the mixture was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane=10% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound. MS 358.22 (M+1)

Workup

  1. concentrationthe mixture was concentrated
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane=10% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-b72451e553414d13842ea17cd33086a7
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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