O-DEMETHYLATION OF OPIOID DERIVATIVES WITH METHANE SULFONIC-ACID METHIONINE - APPLICATION TO THE SYNTHESIS OF NALOXONE AND ANALOGS

被引：17

作者：

ANDRE, JD

DORMOY, JR

HEYMES, A

机构：

[1] Sanofi-Chimie, Sisteron, cedex, Route de Gap

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 16期

关键词：

D O I：

10.1080/00397919208019086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naloxone 2 was obtained by demethylation of N-allylnoroxycodone 1 with methane sulfonic acid/methionine. This reagent is an excellent substitute for boron tribromide. It was used for the synthesis of analogous derivatives with variable results.

引用

页码：2313 / 2327

页数：15

共 30 条

[1] ANDRE JD, 1990, Patent No. 359647
[2] EMETIC ACTIVITY OF N-SUBSTITUTED NORAPOMORPHINES
ATKINSON, ER
BULLOCK, FJ
GRANCHELLI, FE
ARCHER, S
ROSENBERG, FJ
TEIGER, DG
NACHOD, FC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (10) : 1000 - 1003
[3] BADET B, 1979, TETRAHEDRON LETT, P1101
[4] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .3. ALCOHOLS OF 6,14-ENDO-ETHENOTETRAHYDROORIPAVINE SERIES AND DERIVED ANALOGS OF N-ALLYLNORMORPHINE AND -NORCODEINE
BENTLEY, KW
HARDY, DG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) : 3281 - &
[5] CLEAVAGE OF ETHERS
BHATT, MV
KULKARNI, SU
[J]. SYNTHESIS-STUTTGART, 1983, (04): : 249 - 282
[6] THE CLEAVAGE OF ETHERS
BURWELL, RL
[J]. CHEMICAL REVIEWS, 1954, 54 (04) : 615 - 685
[7] Casy A. F., 1986, OPIOID ANALGESICS CH
[8] ANALGESICS .1. SYNTHESIS AND ANALGESIC PROPERTIES OF N-SEC-ALKYL-ANDN-TERT-ALKYLNORMORPHINES
DEGRAW, JI
LAWSON, JA
CRASE, JL
JOHNSON, HL
ELLIS, M
UYENO, ET
LOEW, GH
BERKOWITZ, DS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (05) : 415 - 422
[9] REGIOSELECTIVE CLEAVAGE OF AROMATIC METHYL ETHERS BY METHANESULPHONIC ACID IN PRESENCE OF METHIONINE
FUJII, N
IRIE, H
YAJIMA, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20): : 2288 - 2289
[10] APORPHINES .27. MECHANISTIC ASPECTS OF THE REARRANGEMENT OF THEBAINE AND CODEINE ANALOGS IN METHANESULFONIC-ACID - IMPROVED METHOD FOR SYNTHESIS OF N-ALKYLATED APORPHINES
GRANCHELLI, FE
FILER, CN
SOLOWAY, AH
NEUMEYER, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) : 2275 - 2278

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