Potassium sodium tartarate → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester
Reaction equation
C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[C:18]([O:22][C:23]([NH:25][C:26]1[S:27][CH:28]=[C:29]([C:31](OCC)=[O:32])[N:30]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>ClCCl>[C:18]([O:22][C:23]([NH:25][C:26]1[S:27][CH:28]=[C:29]([CH2:31][OH:32])[N:30]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
A 1.0M diisobutylaluminium hydride toluene solution (142 ml) was added dropwise to a stirred solution of ethyl 2-(t-butoxycarbonylamino)-1,3-thiazole-4-carboxylate (14.9 g) in dichloromethane (250 ml) under cooling at −70° C. After the mixture was stirred successively at −78° C. for 2 hours and at 0° C. for 1 hour, an aqueous potassium sodium tartrate solution was added carefully to the mixture, and the whole was further stirred for 2 hours. The mixture was filtered using dichloromethane, and the filtrate was partitioned between dichloromethane and water. The organic layer was separated and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded a crude product of [2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methanol (9.2 g). The product thus obtained was treated with manganese dioxide (70 g) in dichloromethane (300 ml) with stirring at room temperature.
Workup
- stirringthe whole was further stirred for 2 hours
- filtrationThe mixture was filtered
- customthe filtrate was partitioned between dichloromethane and water
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-9435bca86f634216869aa7c65674910a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829580B2
Reaction notes
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