150323-34-5

Basic information

• Product Name: 1,4-Piperazinedicarboxylic acid, 2-[[(1,1-dimethylethyl)amino]carbonyl]-, 4-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (S)-
• CAS NO: 150323-34-5
• Molecular Formula: C22H33N3O5
• Molecular Weight: 419.521
• Mol File: 150323-34-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,4-Piperazinedicarboxylic acid, 2-[[(1,1-dimethylethyl)amino]carbonyl]-, 4-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Piperazinedicarboxylic acid, 2-[[(1,1-dimethylethyl)amino]carbonyl]-, 4-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (S)-(150323-34-5)
• EPA Substance Registry System: 1,4-Piperazinedicarboxylic acid, 2-[[(1,1-dimethylethyl)amino]carbonyl]-, 4-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (S)-(150323-34-5)

Safety Data

• Hazardous Substances Data: 150323-34-5(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 150323-35-6 t-butyl (S)-3-(tert-butylcarbamoyl)-piperazine-1-carboxylate 
• 848482-93-9 (S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 171504-92-0 5-tert-Butylcarbamoyl-2,3-dihydro-pyrazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester 
• 75-64-9 tert-butylamine 
• 150407-69-5 [2S]-1-benzyloxycarbonyl-4-t-butoxycarbonylpiperazine-2-carboxylic acid 

Downstream Products

• 189349-69-7 (S)-4-[(benzyloxy)carbonyl]-3-(1,1-dimethylethylamino) carbonyl piperazine 
• 150323-37-8 N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide 
• 174139-99-2 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid 
• 1027528-21-7 (S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 150323-36-7 dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone 
• 150378-17-9 indinavir 
• 150323-38-9 [14C]-N-Dealkyl Indinavir 
• 189349-50-6 L-765314 
• 150323-35-6 t-butyl (S)-3-(tert-butylcarbamoyl)-piperazine-1-carboxylate 

Relevant articles and documents

Asymmetric hydrogenation of 1,4,5,6-tetrahydropyrazine-2-(N-tert- butyl)carboxamide catalyzed by trans-chelating chiral diphosphine-rhodium complexes

Highly enantioselective hydrogenation of 1,4,5,6-tetrahydropyrazine-2- (N-tert-butyl)carboxamide (2) was accomplished by a rhodium complex coordinated with a chiral diphosphine TRAP ligand, which is possible to chelate to a transition metal atom in a trans-manner. Of particular interest is that (R,R)-(S,S)-i-BuTRAP gave 97% ee of the corresponding piperazine-2- carboxylic acid derivative (3) with (S) configuration, while the hydrogenation with (R,R)-(S,S)-MeTRAP-rhodium catalyst provided (R)-3 with up to 85% ee. 31P NMR studies of behavior of i-Bu- and MeTRAP-rhodium catalysts during the reaction suggest that the asymmetric hydrogenation of 2 with TRAPs may involve two competitive reaction pathways, giving their respective enantiomeric products 3.

Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir

Hydrogenation of tetrahydropyrazine 4g with [(R)-BINAP(COD)Rh]TfO gave piperazine 6g in 96% yield and 99% ee. Simple hydrogenolytic deprotection and crystallization afforded the key chiral (S)-N-Boc-piperazine MK-639 intermediate I in high yield and enant