Sodium Iodide → HCID 67271485, compound

HRID 250849Notes

Reaction equation

HRID 250849 reaction equation
[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:19]=2[OH:30])[CH:15]=[CH:16][CH:17]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:19]=2[O:30][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:15]=[CH:16][CH:17]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67271485HCID 67271485, compoundYield 114.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 300 mg (0.703 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate (prepared in Example 15f), 319 mg (2.11 mmol, 3 eq) of 1-bromo-3-methylbutane and 583 mg (4.22 mmol, 6 eq) of potassium carbonate in the presence of 42 mg (0.281 mmol, 0.4 eq) of sodium iodide in 10 ml of methyl ethyl ketone is refluxed for 21 hours. The insoluble matter is filtered off and the solvent is evaporated off. 400 mg of methyl 3-[3′-(3-heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoate are obtained in the form of a yellowish oil. Quantitative yield.

Workup

  1. filtrationThe insoluble matter is filtered off
  2. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-0d6a4b2fbbcb4ed2b9cc50e0dc6c516c
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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