Sodium Iodide → HCID 67272748, compound

HRID 250847Notes

Reaction equation

HRID 250847 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][O:35][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][O:35][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 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67272748HCID 67272748, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 200 mg (0.47 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate, 200 mg (1.36 mmol, 3 eq) of 2-bromoethylmethyl ether and 390 mg (2.82 mmol, 6 eq) of potassium carbonate in the presence of 28 mg (0.188 mmol, 0.4 eq) of sodium iodide in 8 ml of methyl ethyl ketone is refluxed for 15 hours. The insoluble matter is filtered off and the solvent is evaporated off. The oil obtained is chromatographed on silica gel (10 g FlashSmart column) eluted with 40/60 heptane/ethyl acetate. 223 mg of methyl 3-[3′-(3-heptyl-1-methylureido)-2-(2-methoxyethoxy)biphenyl-4-yl]propanoate are obtained in the form of a yellowish oil. Yield=98%

Workup

  1. filtrationThe insoluble matter is filtered off
  2. customthe solvent is evaporated off
  3. customThe oil obtained
  4. customis chromatographed on silica gel (10 g FlashSmart column)
  5. washeluted with 40/60 heptane/ethyl acetate

Sources & evidence

ORD record
ord-c1014115bf6a456a9b5988a300a0b47e
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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