Hydrochloric Acid → {4-[3-(4-Fluoro-benzyloxy)-5-(3-morpholin-4-yl-prop-1 ynyl)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

HRID 549596Notes

Reaction equation

HRID 549596 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]#[C:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:18]=[C:17]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:16]=2)=[CH:9][C:8]=1[CH3:39])C.[OH-].[Na+].Cl>C(O)C>[F:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][O:30][C:17]2[CH:16]=[C:15]([CH:20]=[C:19]([C:21]#[C:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:18]=2)[CH2:14][S:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:40])=[O:3])=[C:8]([CH3:39])[CH:9]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67171132{4-[3-(4-Fluoro-benzyloxy)-5-(3-morpholin-4-yl-prop-1 ynyl)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester

Product 1

HCID 16036543{4-[3-(4-Fluoro-benzyloxy)-5-(3-morpholin-4-yl-prop-1 ynyl)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{4-[3-(4-Fluoro-benzyloxy)-5-(3-morpholin-4-yl-prop-1ynyl)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester (150 mg; 0.30 mmol) was dissolved in ethanol (20 mL), and aqueous 1 N sodium hydroxide (3 mL) was added. The reaction mixture was stirred for 1 h, acidified with 1 N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic phase was dried and evaporated to dryness. Yield: 190 mg. HPLC-MS: m/z: 536.1 (M+); Rt: 1.76 min.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-87b772d762804c4ba5b0ddcf4409f7a6
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

Loading…