Hydrochloric Acid → 2-Methoxymethyl-thiazolo[5,4-b]pyridin-6-yl-carboxylic acid

HRID 50336Notes

Reaction equation

HRID 50336 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[N:13]=[C:12]([CH2:14][O:15][CH3:16])[S:11][C:8]2=[N:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>C(O)C>[CH3:16][O:15][CH2:14][C:12]1[S:11][C:8]2[C:7]([N:13]=1)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18412416Methyl 2-methoxymethyl-thiazolo[5,4-b]pyridine-6-carboxylate

Product 1

HCID 184124392-Methoxymethyl-thiazolo[5,4-b]pyridin-6-yl-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.1 g (4.62 mmol) of methyl-2-methoxymethylthiazolo[5,4-b]pyridine-6-carboxylate and 9.2 mL of 2N sodium hydroxide solution were stirred into 50 mL of ethanol for one hour at room temperature. Then 9.2 mL of 2N hydrochloric acid were added, the alcohol was distilled off, and it was diluted with 20 mL of water. The aqueous phase was acidified with concentrated hydrochloric acid whilst cooling with ice, the beige precipitate formed was filtered off, then washed with water and dried. Yield: 1.03 g (100% of theory); Rf value: 0.10 (silica gel; ethyl acetate/petroleum ether=3:7).

Workup

  1. distillationthe alcohol was distilled off
  2. additionit was diluted with 20 mL of water
  3. temperaturewhilst cooling with ice
  4. customthe beige precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-71ae40c96c0c4e09b62a60be1f2d0b35
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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