(1R,4S)-4-Amino-2-cyclopentene-1-carboxylic Acid Methyl Ester Hydrochloride

CAS: 426226-35-9

Ref. TR-A596515

Product Information

• Name: (1R,4S)-4-Amino-2-cyclopentene-1-carboxylic Acid Methyl Ester Hydrochloride
• Synonyms: Methyl (1R,4S)-4-Aminocyclopent-2-ene-1-carboxylate Hydrochloride, 2-Cyclopentene-1-carboxylic acid, 4-amino-, methyl ester, hydrochloride
• Brand: TRC

Description

Applications (1R,4S)-4-Amino-2-cyclopentene-1-carboxylic Acid Methyl Ester Hydrochloride is an intermediate used in the synthesis of ent-Abacavir (A105015), which is an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Chemical properties

• Molecular weight: 141.17 + 36.46
• Formula: C₇H₁₁NO₂•HCl
• Color/Form: Neat
• InChI: InChI=1S/C7H11NO2.ClH/c1-10-7(9)5-2-3-6(8)4-5;/h2-3,5-6H,4,8H2,1H3;1H/t5-,6+;/m0./s1
• InChI key: InChIKey=SWYRZYIXFKDJEK-RIHPBJNCSA-N
• SMILES: COC(=O)[C@H]1C=C[C@@H](N)C1.Cl