tert-Butyl methyl ether → Anticancer agent 73

HRID 1905518Notes

Reaction equation

HRID 1905518 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.ClCC1C=[C:23]([CH3:25])[O:22]N=1.C([O:30]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:22][CH2:23][CH3:25])=[O:30])[N:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 27357633-(Chloromethyl)-5-methyl-1,2-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-b45976e1704e44d9b15c212d4bff921f
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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