Imidazole → HCID 68509347, compound

HRID 1947084Notes

Reaction equation

HRID 1947084 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][NH:10][CH:11]1[CH:15]([OH:16])[CH2:14][N:13]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:32][C:33]([Si:36](Cl)([CH3:38])[CH3:37])([CH3:35])[CH3:34].CCOC(C)=O>CN(C=O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][NH:10][CH:11]1[CH:15]([O:16][Si:36]([C:33]([CH3:35])([CH3:34])[CH3:32])([CH3:38])[CH3:37])[CH2:14][N:13]([C:17](=[O:25])[C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 68515219HCID 68515219, compound

Product 1

HCID 68509347HCID 68509347, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {2-[1-(4-chloro-benzoyl)-4-hydroxy-pyrrolidin-3-ylamino]ethyl}-carbamic acid tert-butyl ester (750 mg, 1.95 mmol) in DMF (0.25 mL) at 0° C., was added imidazole (663 mg, 9.15 mmol) and TBDMSCl (309 mg, 2.05 mmol). The reaction mixture was stirred for 2 days. EtOAc (5 mL) was added. The organic phase was washed with Sat. NH4Cl, dried over NkSO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate: MeOH: 10:1) to give the desired product (389 mg, 40% yield) as a colorless oil. MS: (ESI), M/Z, 498 (M+1). Retention time: 2.21 min (FA-polar).

Workup

  1. washThe organic phase was washed with Sat. NH4Cl
  2. customdried over NkSO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Ethyl acetate: MeOH: 10:1)

Sources & evidence

ORD record
ord-2227c178705a41e7ab866030e9610792
Source dataset
uspto-grants-2013_03
Patent number
US08399455B2

Reaction notes

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