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【结 构 式】

【分子编号】69402

【品名】(R)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-3-phenylpropanoate

【CA登记号】

【 分 子 式 】C27H36N2O5

【 分 子 量 】468.59332

【元素组成】C 69.21% H 7.74% N 5.98% O 17.07%

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:(XIX)

The tripeptide benzyl ester precursor (IV) is prepared by the following procedure. Condensation of N-Boc-L-leucine (X) with L-phenylalanine benzyl ester (XVIII) in the presence of DIEA, HOBt and PyBOP in acetonitrile gives the protected dipeptide (XIX), which upon deprotection by means of TFA in CH2Cl2 yields dipeptide (XX). Without isolation, intermediate (XX) is then condensed with N-Boc-L-homophenylalanine (XIV) in the presence of DEEA (diethyl-aminoethanol), HOBt and PyBOP in acetonitrile to provide protected tripeptide (XXI) , which is finally N-deprotected by means of TFA in CH2Cl2 .

1 Smyth, M.S., Laidig, G.J. (Proteolix, Inc.). Compounds for proteasome enzyme inhibition. CA 2589765, EP 1781688, JP 2008509166, US 2009131421, WO 2006017842.
2 Smyth, M.S., Laidig, G.J., Borchardt, R.T. et al. (Proteolix, Inc.). Compounds for proteasome enzyme inhibition. EP 1745064, JP 2008501637, US 2005245435, US 2008200398, US 7232818, WO 2005105827.
3 Smyth, M.S., Laidig, G.J. (Proteolix, Inc.). Compounds for enzyme inhibition. US 2006030533, US 7417042.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 69393 (R)-benzyl 2-((S)-2-((R)-2-amino-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate 2,2,2-trifluoroacetate C32H39N3O4.C2HF3O2 详情 详情
(X) 23663 (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid;N-Boc-L-leucine C11H21NO4 详情 详情
(XIV) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(XVIII) 27693 benzyl (2S)-2-amino-3-phenylpropanoate;L-phenylalanine benzyl ester C16H17NO2 详情 详情
(XIX) 69402 (R)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-3-phenylpropanoate C27H36N2O5 详情 详情
(XX) 69403 (R)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate 2,2,2-trifluoroacetate C22H28N2O3.C2HF3O2 详情 详情
(XXI) 69404 (6S,9S,12R)-benzyl 12-benzyl-9-isobutyl-2,2-dimethyl-4,7,10-trioxo-6-phenethyl-3-oxa-5,8,11-triazatridecan-13-oate C37H47N3O6 详情 详情
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