Hydrochloric Acid → HCID 68492333, compound

HRID 501770Notes

Reaction equation

HRID 501770 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[C:23]5[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([O:30]C)=[O:29])[C:22]=5[S: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.O.Cl.C(Cl)(Cl)Cl>CO.O1CCCC1.[OH-].[Na+]>[C:36]([CH2:35][CH2:34][C:15]1[CH:14]=[C:13]([C:11](=[O:12])[C:10]2[CH:40]=[CH:41][C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:8][C:9]=2[OH:42])[CH:33]=[CH:32][C:16]=1[O:17][CH2:18][C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([OH:30])=[O:29])[C:22]=2[S:21][CH:20]=1)([OH:38])=[O:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 6212ChloroformHCID 68458741HCID 68458741, compound

Product 1

HCID 68492333HCID 68492333, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.15 g of methyl 3-{[4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-(3-methoxy-3-oxopropyl)phenoxy]methyl}-1-benzothiophene-7-carboxylate was dissolved in a mixed solvent of 10 mL of methanol and 10 mL of tetrahydrofuran, to which 2 mL of a 5M aqueous solution of sodium hydroxide was added at room temperature, and then this mixture was stirred for 30 minutes at the same temperature, followed by addition thereto of 2 mL of water, and this mixture was stirred for another 30 minutes at temperatures of 50 to 60° C. The reaction mixture was cooled to room temperature, to which water was added, and then adjusted to pH 2 with 6M hydrochloric acid. Chloroform was added to this reaction mixture, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water, the organic phase was separated and the solvent was distilled out thereof under reduced pressure. The resultant residue was washed with hexane to yield 1.00 g of 3-({2-(2-carboxyethyl)-4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]phenoxy}methyl)-1-benzothiophene-7-carboxilic acid as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. additionfollowed by addition
  3. additionwas added
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. customthe organic phase was separated
  7. distillationthe solvent was distilled out thereof under reduced pressure
  8. washThe resultant residue was washed with hexane

Sources & evidence

ORD record
ord-a2cb9a3a43294d498bfde42c924f8b82
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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