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【结 构 式】

【分子编号】65046

【品名】4-allyl 3-(tert-butyl) (4R)-5,5-dimethyl-1,3-thiazolidine-3,4-dicarboxylate

【CA登记号】

【 分 子 式 】C14H23NO4S

【 分 子 量 】301.40696

【元素组成】C 55.79% H 7.69% N 4.65% O 21.23% S 10.64%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

5,5-Dimethylthiazolidine-4-carboxylic acid (I) is protected as the N-Boc derivative (II), and subsequently treated with allyl bromide (III) and triethylamine to form the allyl ester (IV). Acidic Boc group cleavage in (IV) provides amino ester (V), which is further coupled to the lactone acid (VI) to furnish amide (VII). The allyl ester group of (VII) is then removed by treatment with morpholine and Pd(PPh3)4, yielding acid (VIII). This is then coupled to (3,5-dimethylisothiazol-4-yl)methyl amine (IX) employing EDC/HOAt to afford the corresponding amide (X). Lactone ring opening in (X) by hydrolysis with LiOH gives rise to the hydroxy acid (XI), which is further protected as the silyl ether (XII) employing t-butyldimethylsilyl triflate.

1 Bohn, J.; Lu, Z.; Raghavan, S.; Charest, M.; Stahlhut, M.; Rutkowski, C.A.; Himmelberger, A.L.; Olsen, D.B.; Scheleif, W.A.; Carella, A.; Gabryelski, L.; Jin, L.; Lin, J.H.; Tata, J.R.; Chapman, K.; Synthesis of highly potent HIV protease inhibitors with activity against protease resistant virus. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 205.
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) 34776 (4R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 72778-00-8 C6H11NO2S 详情 详情
(II) 34777 (4R)-3-(tert-butoxycarbonyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid C11H19NO4S 详情 详情
(III) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(IV) 65046 4-allyl 3-(tert-butyl) (4R)-5,5-dimethyl-1,3-thiazolidine-3,4-dicarboxylate C14H23NO4S 详情 详情
(V) 65047 allyl (4R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate C9H15NO2S 详情 详情
(VI) 65048 (2S,4R)-4-benzyl-5-oxotetrahydro-2-furancarboxylic acid C12H12O4 详情 详情
(VII) 65049 allyl (4R)-3-{[(2S,4R)-4-benzyl-5-oxotetrahydro-2-furanyl]carbonyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylate C21H25NO5S 详情 详情
(VIII) 65050 (4R)-3-{[(2S,4R)-4-benzyl-5-oxotetrahydro-2-furanyl]carbonyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid C18H21NO5S 详情 详情
(IX) 65059 (3,5-dimethyl-4-isothiazolyl)methanamine; (3,5-dimethyl-4-isothiazolyl)methylamine C6H10N2S 详情 详情
(X) 65060 (4R)-3-{[(2S,4R)-4-benzyl-5-oxotetrahydro-2-furanyl]carbonyl}-N-[(3,5-dimethyl-4-isothiazolyl)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide C24H29N3O4S2 详情 详情
(XI) 65061 (2R,4S)-2-benzyl-5-[(4R)-4-({[(3,5-dimethyl-4-isothiazolyl)methyl]amino}carbonyl)-5,5-dimethyl-1,3-thiazolidin-3-yl]-4-hydroxy-5-oxopentanoic acid C24H31N3O5S2 详情 详情
(XII) 65062 (2R,4S)-2-benzyl-4-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4R)-4-({[(3,5-dimethyl-4-isothiazolyl)methyl]amino}carbonyl)-5,5-dimethyl-1,3-thiazolidin-3-yl]-5-oxopentanoic acid C30H45N3O5S2Si 详情 详情
Extended Information