201730-82-7

Upstream product

• 182160-14-1 2-((S)-1-Hydroxy-2,2-dimethyl-propyl)-3-((S)-2-phenyl-aziridin-1-yl)-3H-quinazolin-4-one 
• 201730-83-8 3-((R)-2-Chloro-2-phenyl-ethylamino)-2-((S)-1-hydroxy-2,2-dimethyl-propyl)-3H-quinazolin-4-one 

Downstream Products

• 137102-65-9 (R)-(2-amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 312532-36-8 {(R)-2-[2-((S)-1-Hydroxy-2,2-dimethyl-propyl)-4-oxo-4H-quinazolin-3-ylamino]-1-phenyl-ethyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

1-(3,4-Dihydro-4-oxoquinazolin-3-yl)aziridines (Q-substituted aziridines): Ring-opening reactions with C-N bond cleavage and preparation of Q-free chirons

The presence of the Q group in ring-opening reactions of N-(Q)-aziridines 3, 4, 5 and 6 has been found to be advantageous in the following ways, (i) nucleophilic ring-opening by cuprate or by azide with inversion of configuration is assisted by the electron-withdrawing character of the Q group, (ii) ring-opening of aziridines 5 or 6 to the corresponding alcohols 36 and 23 with retention of configuration can be accomplished by participation of the Q group: the Q carbonyl oxygen becomes the hydroxy oxygen in the alcohol product, (iii) the combined effects of the electron-withdrawing Q group and ring strain allow preparation of individual aziridine N-invertomers 3 and 4 whose ring-opening with hydrogen chloride in dichloromethane proceeds with complementary stereochemistry. The Q group is also believed to be involved in ring-opening of aziridines 5 and 6 mediated by samarium(III) nitrate hexahydrate with predominant retention of configuration. Reductive removal of the Q group from these ring-opened products gave chirons 12, 19 and 21. The Royal Society of Chemistry 2000.

Ring-opening of chiral N-(3,4-dihydro-4-oxoquinazolin-3-yl)-substituted aziridines (Q*-substituted aziridines): Access to Q*-free chirons

The presence of the quinazolin-4(3H)-one ring (Q*) in N-(Q*)-aziridines facilitates ring-opening by nucleophiles: removal of the Q* group from enantiopure ring-opened products gives useful chirons.