L-Glutamic acid, N-(4-(methylamino)benzoyl)-, 1,5-diethyl ester → N-(3,4-dihydro-2-hydroxymethyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino-2-thenoyl-L-glutamic acid

Participants

Reaction Steps

The process described in Example 3 was repeated using 2-acetoxymethyl-6-bromomethyl-3,4-dihydroquinazolin-4-one (prepared from the 6-methyl compound, which is described in note (5) of Example 4, using the process described in the portion of Example 3 concerned with the preparation of starting materials) in place of 6-bromomethyl-3,4-dihydro-2-methylquinazolin-4-one and, in turn, diethyl N-(5-methylamino-2-theonyl)-L-glutamate and diethyl N-(5-ethylamino-2-thenoyl)-L-glutamate (both of which were prepared as described in note (5) of Example 7) in place of diethyl N-(p-methylaminobenzoyl)-L-glutamate. There were thus obtained N-5-[N-(3,4-dihydro-2-hydroxymethyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino-2-thenoyl-L-glutamic acid, as its monohydrate, m.p. 180°-190° C. and N-{5-[N-(3,4-dihydro-2-hydroxymethyl-4-oxoquinazolin-6-ylmethyl)-N-ethylamino-2-thenoyl}-L-glutamic acid, as its monohydrate, m.p. 148°-153° C.

Provenance & Evidence