207304-86-7

Basic information

• Product Name: (2S,4S)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl
• Synonyms: (2S,4S)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl;Methyl (2S,4S)-1-Cbz-4-aMinopyrrolidine-2-carboxylate hydrochloride
• CAS NO: 207304-86-7
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 314.76466
• Mol File: 207304-86-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,4S)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl(207304-86-7)
• EPA Substance Registry System: (2S,4S)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl(207304-86-7)

Safety Data

• Hazardous Substances Data: 207304-86-7(Hazardous Substances Data)

Usage

General Description

(2S,4S)-1-CBZ-4-amino Pyrrolidine-2-carboxylic acid methylester-HCl, also known as Cbz-L-pyroglutamic acid methyl ester hydrochloride, is a derivative of pyroglutamic acid. It is a compound commonly used in the synthesis of peptides and pharmaceuticals. The (2S,4S) configuration indicates that the molecule contains two chiral centers, making it optically active. The Cbz group is a protecting group commonly used in peptide synthesis to protect the amino group, preventing unwanted side reactions while retaining the desired reactivity of the carboxyl group. The hydrochloride salt form of this compound makes it more stable and easier to work with in laboratory settings. Overall, (2S,4S)-1-CBZ-4-amino Pyrrolidine-2-carboxylic acid methylester-HCl is an important intermediate in the production of various bioactive compounds and pharmaceuticals.

Upstream product

• 113490-74-7 4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 117811-78-6 methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 168263-80-7 methyl (2S,4S)-1-benzyloxycarbonyl-4-tert-butoxycarbonylaminopyrrolidine-2-carboxylate 
• 663948-85-4 tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate 
• 380648-94-2 benzyl (2S,4S)-4-((tert-butoxycarbonyl)amino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 380648-96-4 {1-[2-((2S,4S)-4-tert-Butoxycarbonylamino-2-hydroxymethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid benzyl ester 
• 380648-97-5 {(2S,4S)-4-t-butoxycarbonylamino-1-[(thymin-1-yl)methylcarbonyl]-pyrrolidin-2-yl}methyl 4-nitrophenyl carbonate 
• 380648-98-6 carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester 
• 1321614-25-8 methyl (4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-31-6 methyl (4S)-1-[(2S)-3-(acetylsulfanyl)-2-methylpropanoyl]-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-34-9 (4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-L-proline 
• 1321614-42-9 methyl N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-(4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-45-2 N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-(4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 

Relevant articles and documents

DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE

Provided herein are a dihydropyrimidine compound and use as a medicament, especially application as a medicament used for treating and preventing hepatitis B. Specifically, provided herein is a compound having Formula (I) or (Ia), or a stereisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicament, especially use as a medicament for treating and preventing hepatitis B.

Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones

The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.

Synthesis and evaluation of prolyl carbamate nucleic acids (PrCNA)

Carbamate linked prolyl nucleic acids are obtained in high yield and purity under mild conditions in solution and solid phase. p-Nitrophenylchloroformate is used as the activating reagent for alcohol. Homooligomers of PrCNA do not bind to DNA. The introduction of this modification in PNA sequences destabilizes the triplxes, inspite of enhancement in the base stacking.