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【结 构 式】

【分子编号】26065

【品名】3-isobutylpentanedioic acid

【CA登记号】

【 分 子 式 】C9H16O4

【 分 子 量 】188.22364

【元素组成】C 57.43% H 8.57% O 34%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(XXXIV)

5) The condensation of 3-methylbutanal (XIX) with cyanoacetic acid ethyl ester (XXXII) or cyanoacetamide (XXXIII) by means of dipropylamine in refluxing hexane, followed by treatment with refluxing 6N HCl, gives 3-isobutylglutaric acid (XXXIV). This compound is converted into the corresponding anhydride (XXXV) by treatment with refluxing acetic anhydride. The reaction of the anhydride (XXXV) with NH4OH affords the glutaramic amide (XXXVI), which is submitted to optical resolution with (R)-(+)-1-phenylethylamine, yielding the (S)-enantiomer (XXXVII). Finally, this compound is submitted to a Hoffmann degradation with Br2/NaOH.

1 Newhouse, B.J.; Ibrahim, P.; Burgess, L.E.; et al.; Potent selective nonpeptidic inhibitors of human lung tryptase. Proc Natl Acad Sci USA 1999, 96, 15, 8348.
2 Sobieray, D.M.; Hoekstra, M.S.; Schwindt, M.A.; et al.; Chemical development of CI-1008, an enantiomerically pure anticonvulsant. Org Process Res Dev 1997, 1, 1, 26.
3 Huckabee, B.K.; Sobieray, D.M. (Pfizer Inc.); Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid. WO 9638405 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIX) 26052 3-methylbutanal 590-86-3 C5H10O 详情 详情
(XXXII) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(XXXIII) 12122 Cyanoacetamide; 2-Cyanoacetamide 107-91-5 C3H4N2O 详情 详情
(XXXIV) 26065 3-isobutylpentanedioic acid C9H16O4 详情 详情
(XXXV) 26066 4-isobutyldihydro-2H-pyran-2,6(3H)-dione C9H14O3 详情 详情
(XXXVI) 26067 3-(2-amino-2-oxoethyl)-5-methylhexanoic acid C9H17NO3 详情 详情
(XXXVII) 26068 (3R)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid C9H17NO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

 

1 Zhang GS, Yang XP, Ma, YQ, et aL. 2006. Method for preparation of Pregabalin and its intermediate. W0 2006136087.(本专利属于Nhwa Pharma Corporation, Peop Rep China)
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(II) 26052 3-methylbutanal 590-86-3 C5H10O 详情 详情
(III) 66601 diethyl 3-isobutylpentanedioate   C13H24O4 详情 详情
(IV) 26065 3-isobutylpentanedioic acid C9H16O4 详情 详情
(V) 66602 4-isobutylpiperidine-2,6-dione   C9H15NO2 详情 详情
(VI) 26056 3-(aminomethyl)-5-methylhexanoic acid 130912-52-6 C8H17NO2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(I)

 

1 Chen A, Zhang JJ. 2005. Synthesis of Pregabalin. 中国医药工业杂志,35: 195~196
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 26065 3-isobutylpentanedioic acid C9H16O4 详情 详情
(II) 26066 4-isobutyldihydro-2H-pyran-2,6(3H)-dione C9H14O3 详情 详情
(III) 66612 3-(2-(aminooxy)-2-oxoethyl)-5-methylhexanoic acid   C9H17NO4 详情 详情
(IV) 26056 3-(aminomethyl)-5-methylhexanoic acid 130912-52-6 C8H17NO2 详情 详情
Extended Information