Trityl chloride → HCID 58739232, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2 °C
Procedure
A mixture of 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.0 g, 5.4 mmol) in N,N-dimethylformamide at 25° C. was treated with triethylamine (1.89 mL, 13.5 mmol) and triphenylmethylchloride (1.66 g, 5.94 mmol). The reaction was stirred at 2° C. for 2 days. At this time, the reaction was concentrated in vauco. The residue was dissolved in dichloromethane (100 mL) and was washed with a 1N aqueous hydrochloric acid solution (1×20 mL), a saturated aqueous sodium bicarbonate solution (1×20 mL), and a saturated aqueous sodium chloride solution (1×20 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid ethyl ester (2.3 g, quant.). The product was used without further purification: LR-MS for C26H24N2O2S (M−H)+ at m/z=427.
Workup
- concentrationAt this time, the reaction was concentrated in vauco
- dissolutionThe residue was dissolved in dichloromethane (100 mL)
- washwas washed with a 1N aqueous hydrochloric acid solution (1×20 mL)
- dry with materialThe organics were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-be258d042b964ab48ae2133d1c69f4fa
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135475B2
Reaction notes
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