75176-19-1

Basic information

• Product Name: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester
• Synonyms: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester
• CAS NO: 75176-19-1
• Molecular Weight: 293.32
• Mol File: 75176-19-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester(75176-19-1)
• EPA Substance Registry System: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester(75176-19-1)

Safety Data

• Hazardous Substances Data: 75176-19-1(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 75176-20-4 N-(benzyloxycarbonyl)-cis-4-methoxy-L-proline 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 67-56-1 methanol 

Downstream Products

• 1109790-64-8 (2S,4S)-benzyl 2-(6-fluoropyridin-3-ylcarbamoyl)-4-methoxypyrrolidine-1-carboxylate 
• 1109790-61-5 (2S,4S)-benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 871979-42-9 3-[3-((4S)-methoxy-(2S)-pyrrolidinyl)-5-isoxazol]propionic acid benzyl ester hydrochloride 
• 871979-07-6 5-[(1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester 
• 871979-08-7 3-[2-(1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)-5-oxazolyl]propionic acid methyl ester 
• 871979-10-1 3-[2-[1-[2,5-dichloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetyl]-(4S)-methoxy-(2S)-pyrrolidinyl]-5-oxazolyl]propionic acid methyl ester 
• 189069-17-8 4-cis-methoxy L-proline methyl ester 
• 1403562-46-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-triethylsilyloxymethylpyrrolidine 
• 871810-55-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-trimethylsilyloxymethylpyrrolidine 
• 200184-69-6 (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde 
• 871810-57-0 trans-4-[1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid ethyl ester 
• 1403562-48-0 C₂₃H₃₃NO₆ 
• 858971-57-0 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol 
• 75176-20-4 N-(benzyloxycarbonyl)-cis-4-methoxy-L-proline 

Relevant articles and documents

A concise synthesis of a very late antigen-4 antagonist trans-4-[1-[[2,5-dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S) -methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid via reductive etherification

This contribution describes a concise synthesis to ethyl trans-[(4S)-methoxy-(25)-pyrrolidinylmethoxy] cyclohexanecarboxylate (2b) as a key intermediate of very late antigen-4 (VLA-4) antagonist trans-4-[1-[[2,5- dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S)-methoxy-(2S) -pyrrolidinylmethoxy] cyclohexanecarboxylic acid (1). The synthesis employs a reductive etherification as a key reaction using (2S,4S)-1-benzyloxycarbonyl-4- methoxypyrrolidine-2-carboxyaldehyde (12) and trans-4- triethylsilyloxycyclohexanecarboxilic acid ethyl ester (13b). This synthesis provides 2b in 6 steps with 38% overall yield from commercially available starting material.

VLA-4 INHIBITOR

An object of the present invention is to provide a compound which selectively inhibits binding of a ligand and ±421 integrin (VLA-4), a process for producing the compound, and a medicament containing the compound. A compound represented by the formula (I) etc. orasaltthereof, a process for producing the compound or a salt thereof, a medicament containing the compound or a salt thereof, as well as a preventive and/or a therapeutic agent for a disease caused by cell adhesion, for example, inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory bowel disease and rejection reaction at transplantation, containing the compound or a salt thereof as a primary component. [wherein Y 1 represents a divalent aryl group etc. , V 1 represents an aryl group etc., and R 11 to R 14 represent H, OH or a halogen atom etc.]

VLA-4 INHIBITOR

A compound which selectively inhibits bonding between a ligand and α4β1 integrin (VLA-4); a process for producing the compound; and a medicine containing the compound. The compound is one represented by, e.g., the formula (I) or a salt thereof. Also provided is a preventive and/or therapeutic agent which contains the compound or salt as a major component and is effective against diseases attributable to cell adhesion, such as, e.g., inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory intestinal disease, and rejection reaction in transplantation. (In the formula, Y1 represents arylene, etc.; V1 represents aryl, etc.; and R11 to R14 each represents H, OH, halogeno, etc.)