Hydrochloric Acid → HCID 11599069, compound

HRID 2428072Notes

Reaction equation

HRID 2428072 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:18]=[C:17]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=3)[N:16]=[C:15]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=3)[CH:14]=2)=[CH:8][C:7]=1[CH3:39].Cl.O.C(OCC)(=O)C>C1COCC1.C(O)C.[OH-].[Na+]>[OH:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]#[C:19][C:17]2[CH:18]=[C:13]([S:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:40])=[O:2])=[C:7]([CH3:39])[CH:8]=3)[CH:14]=[C:15]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=3)[N:16]=2)=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 67266527HCID 67266527, compound

Product 1

HCID 11599069HCID 11599069, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

{4-[2,6-Bis-(4-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (150 mg; 0.27 mmol) was dissolved in a mixture of THF and ethanol (1:1) (10 ml) and 1N sodium hydroxide (1.5 ml) was added. The reaction mixture was stirred for about 1 h and 1N aqueous hydrogen chloride (3 ml), water (10 ml) and ethyl acetate (20 ml) was added. The organic phase was separated from the aqueous phase and the aqueous phase was extracted with ethyl acetate (10 ml). The pooled organic phases were washed with water (10 ml), dried and evaporated. During the evaporation a solid was formed which was filtered off and dried to give {4-[2,6-bis-(4-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-2-methyl-phenoxy}-acetic acid. Yield: 51 mg.

Workup

  1. additionwas added
  2. customThe organic phase was separated from the aqueous phase
  3. extractionthe aqueous phase was extracted with ethyl acetate (10 ml)
  4. washThe pooled organic phases were washed with water (10 ml)
  5. customdried
  6. customevaporated
  7. customDuring the evaporation a solid
  8. customwas formed which
  9. filtrationwas filtered off
  10. customdried

Sources & evidence

ORD record
ord-3ac2df8617e747508bc250cbbb472b54
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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