Sodium Hydroxide → Methyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylate

HRID 908631Notes

Reaction equation

HRID 908631 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH2:11][O:12]C)=[O:4].B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH2:11][OH:12])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 25220423Methyl 2-amino-4-(methoxymethyl)thiazole-5-carboxylate

Product 1

HCID 12308572Methyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (4.68 g) obtained in Step 2 was suspended in dichloromethane (160 ml), and boron tribromide (1.0M dichloromethane solution, 35 ml) was added dropwise with stirring under ice-cooling. The reaction mixture was stirred under ice-cooling for 90 min, 4N aqueous sodium hydroxide solution (26 ml) was added dropwise with stirring under ice-cooling, and the mixture was stirred at room temperature for 30 min. The precipitated solid was collected by filtration, washed with water and acetone, and dried to give the title compound (3.15 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred under ice-
  3. temperaturecooling for 90 min
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature for 30 min
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with water and acetone
  9. customdried

Sources & evidence

ORD record
ord-6baca62039b94d15869f4dd323fb72b2
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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