Hydrochloric Acid → HCID 78322616, compound

HRID 1051300Notes

Reaction equation

HRID 1051300 reaction equation
[OH:1][CH2:2][CH:3]([CH3:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([O:20]CC)=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][C:7]=1[N:23]1[CH:27]=[N:26][N:25]=[N:24]1.[OH-].[Na+].Cl.O>O1CCCC1.CO>[OH:1][CH2:2][CH:3]([CH3:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([OH:20])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][C:7]=1[N:23]1[CH:27]=[N:26][N:25]=[N:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118555060HCID 118555060, compound

Product 1

HCID 78322616HCID 78322616, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution was prepared by dissolving 34.1 mg of ethyl 2-[4-(3-hydroxy-2-methylpropoxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate in 1.0 mL of a mixed solution of tetrahydrofuran/methanol=1/1. A reaction mixture solution prepared by adding 0.2 mL of 2 M sodium hydroxide aqueous solution to the solution was stirred at room temperature for 3 hours. After the addition of 0.2 mL of 2 M hydrochloric acid to the reaction mixture solution under stirring, 3 mL of water was added and extraction was performed using 4 mL of ethyl acetate. The organic layer was concentrated, followed by purifying by a conventional method to obtain 15.4 mg of 2-[4-(3-hydroxy-2-methylpropoxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid.

Workup

  1. customA solution was prepared
  2. customA reaction mixture solution prepared
  3. stirringunder stirring
  4. extractionextraction
  5. concentrationThe organic layer was concentrated
  6. customby purifying by a conventional method

Sources & evidence

ORD record
ord-d2b3bec9493e4201af12c8327c91fffa
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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