Hydrochloric Acid → HCID 16034861, compound

HRID 549601Notes

Reaction equation

HRID 549601 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:17]=[C:16]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:15]=2)=[CH:9][C:8]=1[CH3:37])C.[OH-].[Na+].Cl>C(O)C>[CH2:33]([O:32][C:16]1[CH:15]=[C:14]([S:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:38])=[O:3])=[C:8]([CH3:37])[CH:9]=2)[CH:19]=[C:18]([C:20]#[C:21][C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=2)[CH:17]=1)[CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67170655HCID 67170655, compound

Product 1

HCID 16034861HCID 16034861, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{4-[3-Isobutoxy-5-(4-methanesulfonyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester (190 mg; 0.34 mmol) was dissolved in ethanol (10 mL), and aqueous 1 N sodium hydroxide (3 mL) was added. The reaction mixture was stirred for 16 h. acidified with 1 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and evaporated to dryness and purified by prep HPLC (method B). Yield: 110 mg (61%). HPLC-MS: m/z: 525.1 (M+H)+; Rt: 2.55 min.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. custompurified by prep HPLC (method B)

Sources & evidence

ORD record
ord-a6909066c28c4080b5b2f01c4b9884ba
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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