Imidazole → HCID 57974634, compound

HRID 1864685Notes

Reaction equation

HRID 1864685 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].N1C=CN=C1.[Si:23](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([O:10][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 109885451,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-

Product 1

HCID 57974634HCID 57974634, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3R)-N-tert-butyloxycarbonyl-3-hydroxy-2 pyrrolidinecarboxylic acid methyl ester (1D) (736 mg, 3.00 mmol) in DMF (10 mL) at rt was added imidazole (1.02 g, 15.0 mmol), DMAP (12.0 mg), and tert-butydiphenylsilyl chloride (988 mg, 3.60 mmol). After stirring overnight, the reaction mixture was partitioned between H2O and CH2Cl2. The organic layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified via silica gel chromatography (eluting with 30% EtOAc/hexane) to yield compound 1E (1.36 g).

Workup

  1. customthe reaction mixture was partitioned between H2O and CH2Cl2
  2. washThe organic layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel chromatography (eluting with 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-11172e43e9944008b343ce1c565a0a3d
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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