Hydrochloric Acid → 3-(2-Methyl-benzothiazol-6-yl)-propionic acid

HRID 1469651Notes

Reaction equation

HRID 1469651 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1.[OH-].[Na+].Cl>CCO>[CH3:13][C:11]1[S:12][C:8]2[CH:7]=[C:6]([CH2:5][CH2:4][C:3]([OH:16])=[O:2])[CH:15]=[CH:14][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 675056953-(2-Methyl-benzothiazol-6-yl)-propionic acid methyl ester

Product 1

HCID 596082613-(2-Methyl-benzothiazol-6-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Next, to a solution of 3-(2-methyl-benzothiazol-6-yl)-propionic acid methyl ester (150 mg, 1.67 mmol) in EtOH (5 mL) is added aqueous 1M NaOH (5 mL) and the mixture is stirred at room temperature for 2 hours. The solution is acidified to pH 3 with aqueous 1M HCl and is extracted with ethyl acetate. The organic layer is washed with water, brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure and the residue is purified by preparative HPLC using a gradient of 10-100% MeCN/water (0.1% TFA) to give 3-(2-methyl-benzothiazol-6-yl)-propionic acid.

Workup

  1. extractionis extracted with ethyl acetate
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-7ac9f021a5c849ab8239e83c604f4be7
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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