tert-Butyl methyl ether → Anticancer agent 73

HRID 359835Notes

Reaction equation

HRID 359835 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([CH3:16])[N+:14]=2[O-])=[CH:6][CH:5]=1.C[O:19][C:20]1C=CC(C2OC(C)=C(C)N=2)=C[CH:21]=1.C([O:37]C)(C)(C)C>[Zn]>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([C:16]([O:19][CH2:20][CH3:21])=[O:37])[N:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 189829612-(4-Methoxy-phenyl)-4,5-dimethyl-oxazoleHCID 200640232-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide hydrochloride

Product 1

HCID 20064063Anticancer agent 73Yield 61%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

2-(4-Methoxyphenyl)-4-carbethoxy-5-methyloxazole was prepared in 61% yield by zinc dust reduction of the compound of part (a) in accordance with the procedure of Example 89, part (b), and obtained as a crystalline material, m.p. 74°-76° C. (from methyl t-butyl ether).

Sources & evidence

ORD record
ord-bd320bffc23e4aec9011639c9f3e9493
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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