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【结 构 式】

【分子编号】49949

【品名】(4S)-4-ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate

【CA登记号】

【 分 子 式 】C15H15NO6

【 分 子 量 】305.28724

【元素组成】C 59.01% H 4.95% N 4.59% O 31.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIX)

Treatment of (XIII) with aqueous trifluoroacetic acid produced simultaneous ketal group hydrolysis and lactonization, yielding intermediate (XIV). Optionally, basic hydrolysis of the ester groups of (XIII) with LiOH produced the lithium carboxylate salt (XV). Lactonization of (XV) with HOAc in chloroform gave (XVI). The cyclic ketal group of (XVI) was then hydrolyzed with aqueous trifluoroacetic acid to produce the intermediate (XVII). Alternatively, (XVII) was also produced by simultaneous hydrolysis and cyclization of (XV) with aqueous trifluoroacetic acid or by basic hydrolysis of (XIV), followed by acidic treatment. Intermediate (XIX) was prepared by acetylation of (XVI) followed by acidic hydrolysis of the resulting ketal (XVIII).

1 Nomura, S.; Tsujihara, K.; Kawaguchi, T. (Tanabe Seiyaku Co., Ltd.); S type 2-substd. hydroxy-2-indolidinylbutyric ester cpds. and process for preparation thereof. US 6277992 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 49943   C44H48N2O11S 详情 详情
(XIV) 49945 (4S)-4-ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl (3R)-2-([1,1'-biphenyl]-4-ylsulfonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate C35H30N2O8S 详情 详情
(XV) 49946   C18H24LiNO7 详情 详情
(XVI) 49947   C18H23NO6 详情 详情
(XVII) 10841 (4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione C13H13NO5 详情 详情
(XVIII) 49948   C20H25NO7 详情 详情
(XIX) 49949 (4S)-4-ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate C15H15NO6 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XIX)

The title compound was prepared from aminopropiophenone (XXVII) by several procedures. Aldol condensation of (XXVII) with the intermediate pyranoindolizinetrione (XVII) with concomitant Friedlander quinoline synthesis under acidic conditions furnished the camptothecin derivative (XXVIII). Optionally, (XXVIII) was also obtained by condensation of (XXVII) with intermediate ketone (XIX), followed by basic hydrolysis of the resultant lactone-ester (XXIX) and subsequent relactonization under acidic conditions. Finally, acid cleavage of the N-Boc group of (XXVII) yielded the title compound.

1 Tsujihara, K.; Kawaguchi, T.; Okuno, S.; Yano, T. (Tanabe Seiyaku Co., Ltd.); Camptothecin derivs.. CA 2182244; EP 0757049; JP 1998072467; US 5837673 .
2 Nomura, S.; Tsujihara, K.; Kawaguchi, T. (Tanabe Seiyaku Co., Ltd.); S type 2-substd. hydroxy-2-indolidinylbutyric ester cpds. and process for preparation thereof. US 6277992 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVII) 10841 (4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione C13H13NO5 详情 详情
(XIX) 49949 (4S)-4-ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate C15H15NO6 详情 详情
(XXVII) 49954 tert-butyl 3-(4-amino-3-propionylphenoxy)propylcarbamate C17H26N2O4 详情 详情
(XXVIII) 49955 tert-butyl 3-[[(4S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl]oxy]propylcarbamate C30H35N3O7 详情 详情
(XXIX) 49956 (4S)-9-[3-[(tert-butoxycarbonyl)amino]propoxy]-4,11-diethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-4-yl acetate C32H37N3O8 详情 详情
Extended Information