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
1
Lead Discovery & Optimization Research Laboratories II, Daiichi Sankyo Co. Ltd.
|
Publication type: Journal Article
Publication date: 2015-03-04
scimago Q3
wos Q3
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
22790822
General Chemistry
Drug Discovery
General Medicine
Abstract
This contribution describes a concise synthesis to ethyl trans-[(4S)-methoxy-(2S)-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.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
|
|
|
ChemInform
1 publication, 100%
|
|
|
1
|
Publishers
|
1
|
|
|
Wiley
1 publication, 100%
|
|
|
1
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
1
Total citations:
1
Citations from 2024:
0
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Chiba J. et al. 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 // Chemical and Pharmaceutical Bulletin. 2015. Vol. 60. No. 7. pp. 882-886.
GOST all authors (up to 50)
Copy
Chiba J., Muro F., Setoguchi M., Machinaga N. 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 // Chemical and Pharmaceutical Bulletin. 2015. Vol. 60. No. 7. pp. 882-886.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1248/cpb.c12-00023
UR - https://doi.org/10.1248/cpb.c12-00023
TI - 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
T2 - Chemical and Pharmaceutical Bulletin
AU - Chiba, Jun
AU - Muro, Fumihito
AU - Setoguchi, Masaki
AU - Machinaga, Nobuo
PY - 2015
DA - 2015/03/04
PB - Pharmaceutical Society of Japan
SP - 882-886
IS - 7
VL - 60
PMID - 22790822
SN - 0009-2363
SN - 1347-5223
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Chiba,
author = {Jun Chiba and Fumihito Muro and Masaki Setoguchi and Nobuo Machinaga},
title = {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},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2015},
volume = {60},
publisher = {Pharmaceutical Society of Japan},
month = {mar},
url = {https://doi.org/10.1248/cpb.c12-00023},
number = {7},
pages = {882--886},
doi = {10.1248/cpb.c12-00023}
}
Cite this
MLA
Copy
Chiba, Jun, et al. “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.” Chemical and Pharmaceutical Bulletin, vol. 60, no. 7, Mar. 2015, pp. 882-886. https://doi.org/10.1248/cpb.c12-00023.