Imidazole → HCID 69950906, compound

HRID 382313Notes

Reaction equation

HRID 382313 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C@@H:8]([N:15]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:32]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C@@H:8]([N:15]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=2)[CH3:16])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:3]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 20640610HCID 20640610, compound

Product 1

HCID 69950906HCID 69950906, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 4-{N-[2-(3-(S)-hydroxypyrrolidin-1-yl)-1-(S)-phenylethyl]-N-methylamino}benzoate (865 mg, 2.44 mmol) in DMF (10 ml) was added imidazole (1.54 g, 24.4 mmol) and tert-butyidimethylsilylchloride (1.83 g, 12.2 mmol) at 0° C. After 3 hr stirring, saturated NaHCO3 aqueous solution was added to the reaction mixture and extracted with CH2Cl2. The extract was washed with water and brine. dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 40 g, CH2Cl2/MeOH: 100/1-50/1) to give 760 mg (66%) of title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extract was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give brown oil, which
  6. customwas purified by column chromatography (silica gel; 40 g, CH2Cl2/MeOH: 100/1-50/1)

Sources & evidence

ORD record
ord-423475b18a25412783cba35b172f9ba5
Source dataset
uspto-grants-2001_10
Patent number
US06310061B2

Reaction notes

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