Convenient removal of N-tert-butyl from amides with scandium triflate

被引：11

作者：

Mahalingam, AK ^{[1
]}

Wu, XY ^{[1
]}

Alterman, M ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, BMC, SE-75123 Uppsala, Sweden

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 18期

关键词：

D O I：

10.1016/j.tetlet.2006.03.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scandium triflate has been used as a convenient and efficient catalyst for removal of N-tert-butyl from amide groups. A variety of N-tert-butyl aryl and alkyl amides under these conditions gave the corresponding primary amide in high yields. With the use of microwave heating the deprotection reaction could be completed within I h. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3051 / 3053

页数：3

共 16 条

[1] Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O)with alcohols in the presence of magnesium perchlorate.: A new and general route to t-butyl ethers [J].

Bartoli, G ;

Bosco, M ;

Locatelli, M ;

Marcantoni, E ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2005, 7 (03) :427-430

[2] Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds [J].

Chun, BK ;

Song, GY ;

Chu, CK .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4852-4858

[3] TOTAL SYNTHESIS OF 6-DEMETHYL-6-DEOXYTETRACYCLINE [J].

CONOVER, LH ;

KORST, JJ ;

BUTLER, K ;

WOODWARD, RB ;

JOHNSTON, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (16) :3222-&

[4] PREPARATION AND UTILITY OF DIANIONS FROM N-TERT-BUTYLTHIOPHENE-2-SULFONAMIDE [J].

GRAHAM, SL ;

SCHOLZ, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4260-4263

[5]

Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd

[6] Total synthesis of (±)-trachyspic acid and determination of the relative configuration [J].

Hirai, K ;

Ooi, H ;

Esumi, T ;

Iwabuchi, Y ;

Hatakeyama, S .

ORGANIC LETTERS, 2003, 5 (06) :857-859

[7] Design, synthesis and structure-activity relationships of benzoxazinone-based factor Xa inhibitors [J].

Huang, WR ;

Zhang, PL ;

Zuckett, JF ;

Wang, LY ;

Woolfrey, J ;

Song, YH ;

Jia, ZZJ ;

Clizbe, LA ;

Su, T ;

Tran, K ;

Huang, B ;

Wong, P ;

Sinha, U ;

Park, G ;

Reed, A ;

Malinowski, J ;

Hollenbach, SJ ;

Scarborough, RM ;

Zhu, BY .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (03) :561-566

[8]

Kobayashi S, 1999, EUR J ORG CHEM, V1999, P15

[9]

Kocienski P.J., 1994, PROTECTING GROUPS

[10] THE ACID-CATALYSED HETEROLYSIS OF AMIDES WITH ALKYL-NITROGEN FISSION (AAL) [J].

LACEY, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1633-1639

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