170028-72-5

Basic information

• Product Name: (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one
• Synonyms: (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one
• CAS NO: 170028-72-5
• Molecular Weight: 366.46
• Mol File: 170028-72-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one(170028-72-5)
• EPA Substance Registry System: (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one(170028-72-5)

Safety Data

• Hazardous Substances Data: 170028-72-5(Hazardous Substances Data)

Upstream product

• 177574-46-8 dibenzyl ((1R,1'R)-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethane-1,1-diyl))dicarbamate 
• 153223-10-0 (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol 
• 1053712-24-5 ((1R,2S,3S,4R)-1-Benzyl-4-benzyloxycarbonylamino-5-phenyl-2,3-bis-triethylsilanyloxy-pentyl)-carbamic acid benzyl ester 
• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 
• 170028-71-4 N'-((R)-1-{(4S,5S)-5-[(R)-1-(N',N'-Dimethyl-hydrazino)-2-phenyl-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-phenyl-ethyl)-N,N-dimethyl-hydrazine 
• 201230-82-2 carbon monoxide 
• 170870-15-2 (1R,1'R)-1,1'-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethanamine) 
• 78-09-1 orthocarbonic acid tetraethyl ester 
• 77-76-9 2,2-dimethoxy-propane 
• 153223-11-1 (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1053741-29-9 (3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-5,7-bis-(3-nitro-benzyl)-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 180302-27-6 2-Fluoro-5-((3aS,4R,8R,8aS)-4,7,8-tribenzyl-2,2-dimethyl-6-oxo-hexahydro-1,3-dioxa-5,7-diaza-azulen-5-ylmethyl)-benzonitrile 
• 218445-75-1 5-((3aS,4R,8R,8aS)-4,8-Dibenzyl-7-butyl-2,2-dimethyl-6-oxo-hexahydro-1,3-dioxa-5,7-diaza-azulen-5-ylmethyl)-2-fluoro-benzonitrile 
• 188978-02-1 DMP 851 
• 548795-25-1 (3aS,4R,8R,8aS)-5-(3-Amino-1H-indazol-5-ylmethyl)-4,8-dibenzyl-7-butyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 180302-28-7 (3aS,4R,8R,8aS)-5-(3-Amino-1H-indazol-5-ylmethyl)-4,7,8-tribenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 151867-81-1 DMP 323 

Relevant articles and documents

Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

Catalytic carbonylation of functionalized diamines: Application to the core structure of DMP 323 and DMP 450

W(CO)6-catalyzed carbonylation provides an alternative to phosgene or phosgene derivatives such as 1,1-carbonyldiimidazole (CDI) for the conversion of amines to ureas. As an illustration, the core structure of the HIV protease inhibitors DMP 32

Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led te intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed te prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.