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
Reaction equation
C([O:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:17]Br)[CH:12]=2)[N:7]=1)(=O)C.BrCC1C=C2C(=CC=1)N=C(C)[NH:25][C:24]2=O.C(N[C:36]1[S:40][C:39]([C:41](N[C@H](C(OCC)=O)CCC(OCC)=O)=[O:42])=[CH:38][CH:37]=1)C.CNC1C=CC(C([NH:65][C@H:66]([C:74]([O:76]CC)=[O:75])[CH2:67][CH2:68][C:69]([O:71]CC)=[O:70])=O)=CC=1>>[OH:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:17][N:65]([NH:25][CH3:24])[C@:66]([C:41](=[O:42])[C:39]3[S:40][CH:36]=[CH:37][CH:38]=3)([C:74]([OH:76])=[O:75])[CH2:67][CH2:68][C:69]([OH:71])=[O:70])[CH:12]=2)[N:7]=1Participants
Reactant 4
Product 1
Procedure
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.
Sources & evidence
- ORD record
- ord-3154530495aa466ba903f8fda275571e
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081124
Reaction notes
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