tert-Butyl methyl ether → Anticancer agent 73

HRID 2165418Notes

Reaction equation

HRID 2165418 reaction equation
[O:1]1C=CN=[C:2]1[C:6]1C=CC(O)=CC=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:22][C:23]([CH3:27])=[C:24]([CH3:26])[N:25]=2)=[CH:17][CH:16]=1.C([O:32]C)(C)(C)C>[Zn]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[O:22][C:23]([CH3:27])=[C:24]([C:26]([O:1][CH2:2][CH3:6])=[O:32])[N:25]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 189829612-(4-Methoxy-phenyl)-4,5-dimethyl-oxazoleHCID 1356214594-(Oxazol-2-yl)phenol

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-ccb0608a85c94223b827f6279c4788f1
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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