Water → Tert-butyl 5-(hydroxymethyl)thiazol-2-ylcarbamate

HRID 1818953Notes

Reaction equation

HRID 1818953 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:7][CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:14]([O:13][C:11](=[O:12])[NH:10][C:8]1[S:9][C:5]([CH2:3][OH:2])=[CH:6][N:7]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 45117879Methyl 2-((tert-butoxycarbonyl)amino)thiazole-5-carboxylate2×

Product 1

HCID 53397352Tert-butyl 5-(hydroxymethyl)thiazol-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-tert-butoxycarbonylamino-thiazole-5-carboxylic acid methyl ester (compound 62.1; 21.7 mmol) in THF was slowly added LAH (25 mL of a 1.0 M solution in THF). After stirring for 1 hour at room temperature the reaction is cautiously hydrolyzed with the sequential addition of water (0.95 mL), 15% aqueous NaOH (0.95 mL) and additional water (2.85 mL). After stirring for 30 minutes the reaction is filtered through a pad of Celite and the filtrate is dried and concentrated to give (5-hydroxymethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (compound 62.2).

Workup

  1. stirringAfter stirring for 30 minutes the reaction
  2. filtrationis filtered through a pad of Celite
  3. customthe filtrate is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-997af14cbffd4b929ea5c8484b91d9a3
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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