Hydrochloric Acid → (S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)-phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylic acid

HRID 41532Notes

Reaction equation

HRID 41532 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:32])[NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]([O:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:16]=3[O:30][CH3:31])[N:14]=2)[CH:5]=[C:4]([Cl:33])[C:3]=1/[CH:34]=[C:35](\[CH3:41])/[C:36]([O:38]CC)=[O:37].[OH-].[Na+].Cl>C1COCC1.C(O)C>[Cl:33][C:4]1[CH:5]=[C:6]([C:8](=[O:32])[NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]([O:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:16]=3[O:30][CH3:31])[N:14]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1/[CH:34]=[C:35](\[CH3:41])/[C:36]([OH:38])=[O:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59544888HCID 59544888, compound

Product 1

HCID 59544885(S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)-phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylic acidYield 89.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylate (14, 6.76 g) obtained in the fifth step was dissolved in THF (20 mL) and ethanol (20 mL), a 4 mol/L sodium hydroxide aqueous solution (13.5 mL) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was neutralized with hydrochloric acid, and extracted with ethyl acetate. The extraction residue was recrystallized with methanol to obtain (S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylic acid (C-1B, 5.8 g, yield 88%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extraction residue was recrystallized with methanol

Sources & evidence

ORD record
ord-0ee5c6ebea7c4fda94cf29306b7654b1
Source dataset
uspto-grants-2013_09
Patent number
US08530668B2

Reaction notes

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