Hydrochloric Acid → HCID 11533898, compound

HRID 2428073Notes

Reaction equation

HRID 2428073 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][CH:24]=[CH:23][C:22]=3[CH2:27][OH:28])[N:16]=[C:15]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:37][OH:38])[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:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]#[C:19][C:17]1[CH:18]=[C:13]([S:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:40])=[O:2])=[C:7]([CH3:39])[CH:8]=2)[CH:14]=[C:15]([C:29]#[C:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH2:37][OH:38])[N:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 67266612HCID 67266612, compound

Product 1

HCID 11533898HCID 11533898, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

{4-[2,6-Bis-(2-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (51 mg; 0.090 mmol) was dissolved in a mixture of THF and ethanol (2:1) (10 ml) and 1N sodium hydroxide (0.5 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 to dryness. The crude product was purified by prep. HPLC to give {4-[2,6-bis-(2-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-2-methyl-phenoxy}-acetic acid. Yield: 23 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 to dryness
  7. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-8ef50c114e2c48e7b864ca882197a2e3
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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