Hydrochloric Acid → HCID 25123290, compound

HRID 1361097Notes

Reaction equation

HRID 1361097 reaction equation
[OH-].[Li+].[CH2:3]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[C:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH:21]=2)=[CH:13][C:12]=1[O:42][CH3:43])(=[O:9])=[O:8])[CH2:4][CH2:5][CH3:6].O.Cl>O1CCCC1>[CH2:3]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH:21]=2)=[CH:13][C:12]=1[O:42][CH3:43])(=[O:8])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86642717HCID 86642717, compound

Product 1

HCID 25123290HCID 25123290, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.62 ml (0.62 mmol) of 1M lithium hydroxide solution is added to a solution of 181.6 mg (0.31 mmol) of methyl 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-(3-methoxybenzyloxy)phenyl]propanoate in 5 ml of tetrahydrofuran. The reaction mixture is stirred overnight at room temperature. The reaction is treated by adding 10 ml of water, acidified with hydrochloric acid and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. After evaporating off the solvents, the residue is purified by chromatography on a column of silica eluted with a 95/5 dichloromethane/methanol mixture. 162 mg (92%) of 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-(3-methoxybenzyloxy)phenyl]propanoic acid are obtained in the form of a yellow oil.

Workup

  1. additionThe reaction is treated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporating off the solvents
  5. customthe residue is purified by chromatography on a column of silica
  6. washeluted with a 95/5 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-65ee482896c645869ff733beaa5e20f2
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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