Potassium Carbonate → (1-{2-[4-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

HRID 79728

Reaction equation

HRID 79728 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:39])[NH:10][CH:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]1[NH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]#[C:34][Si](C)(C)C)=[CH:29][CH:28]=2)=[CH:25][N:26]=1)=[O:16])[CH:12]([CH3:14])[CH3:13]>CO>[CH3:7][O:8][C:9](=[O:39])[NH:10][CH:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]1[NH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]#[CH:34])=[CH:29][CH:28]=2)=[CH:25][N:26]=1)=[O:16])[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66619941(2-methyl-1-{2-[5-(4-trimethylsilanylethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester

Product 1

HCID 72338228(1-{2-[4-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl esterYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (192 mg) was added to (2-Methyl-1-{2-[5-(4-trimethylsilanylethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester (324 mg) in 7 mL MeOH solution. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated down and purified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexane) to give (1-{2-[5-(4-Ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (234 mg).

Workup

  1. concentrationThe reaction mixture was concentrated down
  2. custompurified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f2bb86ffe8e34e19a6b5cf17c473200d
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Linked notes

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