HCID 86598218, compound → HCID 23021532, compound

HRID 501771Notes

Reaction equation

HRID 501771 reaction equation
[CH:1]1([O:6][C:7]2[CH:41]=[CH:40][C:10]([C:11]([C:13]3[CH:33]=[CH:32][C:16]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=4)=[C:15]([CH2:34][CH2:35][C:36]([O:38]C)=[O:37])[CH:14]=3)=[O:12])=[C:9]([OH:42])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.O1CCCC1.[OH-].[Na+]>[CH:1]1([O:6][C:7]2[CH:41]=[CH:40][C:10]([C:11]([C:13]3[CH:33]=[CH:32][C:16]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=4)=[C:15]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH:14]=3)=[O:12])=[C:9]([OH:42])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 86598218HCID 86598218, compound

Product 1

HCID 23021532HCID 23021532, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.20 g of ethyl (E)-3-(4-{[4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-(3-methoxy-3-oxopropyl)phenoxy]methyl}phenyl)-2-propenoate was dissolved in a mixed solvent of 12 mL of methanol and 12 mL of tetrahydrofuran, to which 2.4 mL of a 20% aqueous solution of sodium hydroxide was added at room temperature, and then this mixture was stirred for one hour at the same temperature. The reaction mixture was concentrated under reduced pressure, to which water was added, and then adjusted to pH 2 with 6M hydrochloric acid. The resultant precipitate was filtered out and washed with water to yield 0.841 g of (E)-3-(4-{[4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-(3-hydroxy-3-oxopropyl)phenoxy]methyl}phenyl)-2-propenoic acid as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which water
  3. additionwas added
  4. filtrationThe resultant precipitate was filtered out
  5. washwashed with water

Sources & evidence

ORD record
ord-06272c91d4e243edb6ac9eb2887a3899
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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