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【结 构 式】

【分子编号】26188

【品名】1-(tert-butyl) 3-ethyl 3-(2-pyridinylmethyl)-1,3-piperidinedicarboxylate

【CA登记号】

【 分 子 式 】C19H28N2O4

【 分 子 量 】348.4424

【元素组成】C 65.49% H 8.1% N 8.04% O 18.37%

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)

Protection of ethyl piperidine-3-carboxylate (I) with di tert-butyl dicarbonate gave carbamate (II), which was alkylated with 2-(chloromethyl)pyridine chloride (III) in the presence of potassium hexamethyldisilazide to afford racemic (IV). Acid deprotection of the Boc group of (IV) yielded amine (V). This was resolved by coupling with (R)-O-acetyl mandelic acid (VI), followed by chromatographic separation of the diastereoisomers. Then, acid hydrolysis of the desired isomer (VII) provided the (S)-piperidine (VIII). Subsequent coupling of (VIII) with N-Boc-D-tryptophan (IX) in the presence of EDC and HOBt gave amide (X). After Boc deprotection of (X), the resulting amine (XI) was coupled with N-Boc-2-aminoisobutyric acid (XII) to produce (XIII). Finally, acid removal of the Boc group of (XIII) furnished the title compound.

1 Schleim, K.D.; Leung, K.; Cheng, K.; Patchent, A.A.; Morriello, G.; Smith, R.; Jacks, T.; Yang, L.; Thiazole-derived potent, highly bioavailable short duration growth hormone secretagogues. Bioorg Med Chem Lett 1999, 9, 13, 1761.
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) 25693 ethyl 3-piperidinecarboxylate 5006-62-2 C8H15NO2 详情 详情
(II) 26186 1-(tert-butyl) 3-ethyl 1,3-piperidinedicarboxylate C13H23NO4 详情 详情
(III) 26187 2-(Chloromethyl)pyridine 4377-33-7 C6H6ClN 详情 详情
(IV) 26188 1-(tert-butyl) 3-ethyl 3-(2-pyridinylmethyl)-1,3-piperidinedicarboxylate C19H28N2O4 详情 详情
(V) 26189 ethyl 3-(2-pyridinylmethyl)-3-piperidinecarboxylate C14H20N2O2 详情 详情
(VI) 26190 (2R)-2-(acetoxy)-2-phenylethanoic acid C10H10O4 详情 详情
(VII) 26191 ethyl (3S)-1-[(2R)-2-(acetoxy)-2-phenylethanoyl]-3-(2-pyridinylmethyl)-3-piperidinecarboxylate C24H28N2O5 详情 详情
(VIII) 26192 ethyl (3S)-3-(2-pyridinylmethyl)-3-piperidinecarboxylate C14H20N2O2 详情 详情
(IX) 16114 N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid 13139-14-5 C16H20N2O4 详情 详情
(X) 26193 ethyl (3S)-1-[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]-3-(2-pyridinylmethyl)-3-piperidinecarboxylate C30H38N4O5 详情 详情
(XI) 26194 ethyl (3S)-1-[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]-3-(2-pyridinylmethyl)-3-piperidinecarboxylate C25H30N4O3 详情 详情
(XII) 18471 N-(tert-butoxycarbonyl)-2-methylalanine 30992-29-1 C9H17NO4 详情 详情
(XIII) 26195 ethyl (3S)-1-[(2R)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)-3-(1H-indol-3-yl)propanoyl]-3-(2-pyridinylmethyl)-3-piperidinecarboxylate C34H45N5O6 详情 详情
Extended Information