Hydrochloric Acid → {4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(3-morpholin-4-yl-prop-1-ynyl)phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid

HRID 1513160Notes

Reaction equation

HRID 1513160 reaction equation
C([O:3][C:4](=[O:40])[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][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:17]=[C:16]([O:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH:15]=2)=[CH:9][C:8]=1[CH3:39])C.[OH-].[Na+].Cl>C(O)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][O:29][C:16]2[CH:15]=[C:14]([S:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:40])=[O:3])=[C:8]([CH3:39])[CH:9]=3)[CH:19]=[C:18]([C:20]#[C:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:17]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67171037{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(3-morpholin-4-yl-prop-1-ynyl)phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid Ethyl Ester

Product 1

HCID 16034863{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(3-morpholin-4-yl-prop-1-ynyl)phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(3-morpholin-4-yl-prop-1-ynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester (190 mg; 0.30 mmol) was dissolved in ethanol (25 mL), and aqueous 1 N sodium hydroxide (5 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, redissolved in dichloromethane and evaporated to dryness. Yield: 250 mg (87%). HPLC-MS: m/z: 552.8 (M+H)+; Rt: 1.90 min.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. dissolutionredissolved in dichloromethane
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9b4e907ed41248a29fe4e4108705e877
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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