Hydrogen Peroxide → 3-[2-(4-Methyl-imidazol-1-yl)-thiazol-4-yl]-3-oxo-propionic acid tert.-butyl ester

HRID 1745545Notes

Reaction equation

HRID 1745545 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[S:8][CH:9]=[C:10]([C:12]([O:14]CC)=O)[N:11]=2)[CH:6]=1.NC1SC=C(C(OCC)=O)N=1.[H-].[Na+].N(C(C)C(OC)OC)=C=S.OS(O)(=O)=O.OO.[C:47]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])(=[O:49])[CH3:48].[Li]>CC(O)=O.CCO.CN(C=O)C>[C:51]([O:50][C:47](=[O:49])[CH2:48][C:12]([C:10]1[N:11]=[C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)[S:8][CH:9]=1)=[O:14])([CH3:54])([CH3:53])[CH3:52]

Participants

11

Reactant 7

HCID 784Hydrogen PeroxideHCID 1118Sulfuric Acid2×HCID 24758Sodium hydrideHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 222247702-Isothiocyanato-1,1-dimethoxy-propaneHCID 22224920Ethyl 2-(4-methyl-imidazol-1-yl)-thiazole-4-carboxylateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 695928423-[2-(4-Methyl-imidazol-1-yl)-thiazol-4-yl]-3-oxo-propionic acid tert.-butyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared from ethyl 2-(4-methyl-imidazol-1-yl)-thiazole-4-carboxylate [prepared from ethyl 2-amino-4-thiazolecarboxylate (CAS-No. [256420-32-3]) by the following synthetic sequence: 1.) NaH, 2-isothiocyanato-1,1-dimethoxy-propane, DMF, 23° C.; 2.) aq. H2SO4, reflux; 3.) EtOH, conc. H2SO4, 23° C.; 4.) 30% H2O2, HOAc, 23° C.] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as a brown oil (8.73 g).

Sources & evidence

ORD record
ord-457aac9237ea4649b2b9b7b26d2a1d05
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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