Potassium Carbonate → Methyl 3-[2-(3-chloropropoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

HRID 250851Notes

Reaction equation

HRID 250851 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].[Cl:32][CH2:33][CH2:34][CH2:35]I.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:32][CH2:33][CH2:34][CH2:35][O:30][C:19]1[CH:20]=[C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:23][C:18]=1[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N:10]([CH3:11])[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:31])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67272211Methyl 3-[2-(3-chloropropoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoateYield 111.4%

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-chloro-3-iodopropane and 583 mg (4.22 mmol, 6 eq) of potassium carbonate in 10 ml of methyl ethyl ketone is refluxed for 7 hours. The insoluble matter is filtered off, the solvent is evaporated off and the oil obtained is chromatographed on silica gel (35 g FlashSmart column) eluted with 60/40 heptane/ethyl acetate. 394 mg of methyl 3-[2-(3-chloropropoxy)-3′-(3-heptyl-1-methylureido)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
  3. customthe oil obtained
  4. customis chromatographed on silica gel (35 g FlashSmart column)
  5. washeluted with 60/40 heptane/ethyl acetate

Sources & evidence

ORD record
ord-a000aaf6e75e491cabc8b097020a6929
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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