Phosphate → 2-(2,4-Dihydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid

HRID 338802

Reaction equation

HRID 338802 reaction equation
P([O-])([O-])([O-])=O.C([O-])(O)=O.[Na+].[OH:11][C:12]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].O.Cl.N[C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][SH:26]>CO>[OH:11][C:12]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:13]=1[C:14]1[S:26][CH2:25][CH:24]([C:27]([OH:29])=[O:28])[N:15]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 23462L-Cysteine hydrochloride monohydrateHCID 516892Sodium BicarbonateHCID 30175202,4-Dihydroxybenzonitrile

Product 1

HCID 1357290882-(2,4-Dihydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acidYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixed solvent including methanol (30 mL) and phosphate buffer solution (20 mL), NaHCO3 (466 mg, 5.55 mmol) was carefully added to a solution including the obtained Compound 101a (0.5 g, 3.70 mmol) and L-cysteine hydrochloride monohydrate (974 mg, 5.55 mmol), and the reaction mixture was refluxed for 10 hours. After methanol was evaporated, the reaction mixture was acidified by using 1 N HCl to increase a pH to 2. The resultant precipitate was filtered, and washed with water to obtain Compound 101b (613 mg, 69%).

Workup

  1. additionwas carefully added to a solution
  2. temperaturethe reaction mixture was refluxed for 10 hours
  3. customAfter methanol was evaporated
  4. temperatureto increase a pH to 2
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-4fe09eae77794646a3a764e6fadf12cc
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Linked notes

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