Water → HCID 86642717, compound

HRID 1361096Notes

Reaction equation

HRID 1361096 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[CH2:11]([S:15]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:30]([OH:40])[CH:29]=2)=[CH:21][C:20]=1[O:41][CH3:42])(=[O:17])=[O:16])[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[CH2:11]([S:15]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:30]([O:40][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:29]=2)=[CH:21][C:20]=1[O:41][CH3:42])(=[O:17])=[O:16])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 86642716HCID 86642716, compound

Product 1

HCID 86642717HCID 86642717, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

68 μl (0.5 mmol) of 3-methoxybenzyl chloride are added to a solution of 200 mg (0.5 mmol) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-hydroxyphenyl)propanoate and 89 mg (0.5 mmol) of potassium carbonate in 5 ml of methyl ethyl ketone, and the reaction medium is then heated at 70° C. for 48 hours. After cooling, water is added and the reaction medium is then extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 120 mg (48%) of methyl 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-(3-methoxybenzyloxy)phenyl]propanoate are obtained.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction medium is then extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-6333582588d247ecb1ab3ed8e964ec33
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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