A convenient, large-scale synthesis of 4′-carboxamido N-Boc-2′,6′-dimethyl-L-phenylalanines

被引：5

作者：

Cai, CZ ^{[1
]}

Breslin, HJ ^{[1
]}

He, W ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Drug Discovery, Spring House, PA 19477 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 28期

关键词：

N-Boc-2; 6; '-dimethyl-L-tyrosine; 4 '-carboxamido N-Boc-2 '; '-dimethyl-L-phertylalanines; palladium-catalyzed carbonylation;

D O I：

10.1016/j.tet.2005.04.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A large-scale synthesis of a series of 4-carboxamido N-Boc-2',6'-dimethyl-L-phenylalanines is described. This method features mild reaction conditions and high chemical yields from commercially available N-Boc-2',6'-dimethyl-L-tyrosine methyl ester. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6836 / 6838

页数：3

共 9 条

[1]

BRESLIN HJ, 2003, Patent No. 2003092688

[2] Dmt and opioid peptides: A potent alliance [J].

Bryant, SD ;

Jinsmaa, Y ;

Salvadori, S ;

Okada, Y ;

Lazarus, LH .

BIOPOLYMERS, 2003, 71 (02) :86-102

[3] PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (33) :3931-3934

[4] (4-Carboxamido)phenylalanine is a surrogate for tyrosine in opioid receptor peptide ligands [J].

Dolle, RE ;

Machaut, M ;

Martinez-Teipel, B ;

Belanger, S ;

Cassel, JA ;

Stabley, GJ ;

Graczyk, TM ;

DeHaven, RN .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (13) :3545-3548

[5]

HENDRICKSON JB, 1973, TETRAHEDRON LETT, V14, P4607

[6] Novel 2′, 6′-dimethyl-L-tyrosine-containing pyrazinone opioid mimetic μ-agonists with potent antinociceptive activity in mice [J].

Jinsmaa, Y ;

Okada, Y ;

Tsuda, Y ;

Shiotani, K ;

Sasaki, Y ;

Ambo, A ;

Bryant, SD ;

Lazarus, LH .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2004, 309 (01) :432-438

[7] Catalytic characteristics of CYP3A4: Requirement for a phenolic function in ortho hydroxylation of estradiol and mono-O-demethylated methoxychlor [J].

Stresser, DM ;

Kupfer, D .

BIOCHEMISTRY, 1997, 36 (08) :2203-2210

[8] A selective method for the preparation of primary amides: Synthesis of Fmoc-L-4-carboxamidophenylalanine and other compounds [J].

Wang, W ;

McMurray, JS .

TETRAHEDRON LETTERS, 1999, 40 (13) :2501-2504

[9] 3-carboxamido analogues of morphine and naltrexone: Synthesis and opioid receptor binding properties [J].

Wentland, MP ;

Lou, RL ;

Dehnhardt, CM ;

Duan, WH ;

Cohen, DJ ;

Bidlack, JM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1717-1721

← 1 →