145280-09-7

Basic information

• Product Name: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>bromoacetate
• CAS NO: 145280-09-7
• Molecular Weight: 392.334
• Mol File: 145280-09-7.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>bromoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>bromoacetate(145280-09-7)
• EPA Substance Registry System: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>bromoacetate(145280-09-7)

Safety Data

• Hazardous Substances Data: 145280-09-7(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 4530-20-5 BOC-glycine 
• 7377-98-2 (-)-menthyl chloroacetate 
• 63254-60-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-aminoacetate 
• 145280-11-1 (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate 

Downstream Products

• 154108-97-1 (S)-3-Acetyl-2-tert-butoxycarbonylamino-4-[(E)-hydroxyimino]-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 154108-96-0 (1R,3R,4S)-menthyl (2S)-N-t-BOC-2-(3,5-dimethyl-4-pyrazolyl)glycinate 
• 145280-13-3 (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)imino>acetate 

Relevant articles and documents

A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids

Co(Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC-3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.

The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives

The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.