Hydrochloric Acid → 2-(3-ethoxy-3-oxopropyl)-4-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate

HRID 2249654

Reaction equation

HRID 2249654 reaction equation
[CH3:1][CH:2]([CH3:33])[CH2:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:19]=2)=[O:14])=[CH:9][C:8]=1[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5].[H-].[Na+].[CH2:36](I)[CH2:37][CH:38]([CH3:40])[CH3:39].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][CH:2]([CH3:33])[CH2:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[N:16]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[CH:17]=[C:18]([C:20](=[O:25])[CH2:21][CH:22]([CH3:23])[CH3:24])[CH:19]=2)=[O:14])=[CH:9][C:8]=1[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 109241-Iodo-3-methylbutaneHCID 24758Sodium hydrideHCID 178165282-(3-ethoxy-3-oxopropyl)-4-{[4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate

Product 1

HCID 178164722-(3-ethoxy-3-oxopropyl)-4-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 0.9 g of 2-(3-ethoxy-3-oxopropyl)-4-{[4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate in 18 ml N,N-dimethylformamide are added 0.12 g of 60% sodium hydride and 0.4 ml of isopentyl iodide successively, and the mixture thus obtained is stirred at 50-60° C. for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 0.7 g of 2-(3-ethoxy-3-oxopropyl)-4-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate is obtained as a white solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-e2824c757c6443cc8fe4518d95ad7541
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Linked notes

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