(2S)-2-amino-N-{(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}-3-phenylpropanamide -Drug Synthesis Database

【结构式】

【分子编号】58551

【品名】(2S)-2-amino-N-{(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}-3-phenylpropanamide

【CA登记号】

【分子式】C₂₄H₃₇BN₂O₃

【分子量】412.38046

【元素组成】C 69.9% H 9.04% B 2.62% N 6.79% O 11.64%

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)

Pinanediol leucine boronate (I) was coupled with N-Boc-L-phenylalanine (II) in the presence of TBTU to afford the dipeptide boronate (III). Acid cleavage of the Boc protecting group of (III), followed by acylation of the resultant amine (IV) with 2-pyrazinecarboxylic acid (V), furnished amide (VI). Finally, deprotection of the boronic acid (VI) was accomplished by two-phase transesterification with isobutylboronic acid.

参考文献中间体

合成目标

【1】 Adams, J.; Behnke, M.; Chen, S.; Cruickshank, A.A.; Dick, L.R.; Grenier, L.; Klunder, J.M.; Ma, Y.T.; Plamondon, L.; Stein, R.L.; Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids. Bioorg Med Chem Lett 1998, 8, 4, 333.
【2】 Adams, J.; Ma, Y.-T.; Stein, R.; Baevsky, M.; Grenier, L.; Plamondon, L. (ProScript, Inc.); Boronic ester and acid cpds., synthesis and uses. JP 1998510245; US 5780454; US 6083903; WO 9613266 .

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)	58549	(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]dec-4-yl]-1-butanamine 2,2,2-trifluoroacetate; (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]dec-4-yl]butylamine 2,2,2-trifluoroacetate	179324-87-9	C₁₅H₂₈BNO₂.CF₃COOH	详情	详情
(II)	12874	(2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine	13734-34-4	C₁₄H₁₉NO₄	详情	详情
(III)	58550	tert-butyl (1S)-1-benzyl-2-({(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}amino)-2-oxoethylcarbamate		C₂₉H₄₅BN₂O₅	详情	详情
(IV)	58551	(2S)-2-amino-N-{(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}-3-phenylpropanamide		C₂₄H₃₇BN₂O₃	详情	详情
(V)	37256	2-pyrazinecarboxylic acid; Pyrazinoic acid	98-97-5	C₅H₄N₂O₂	详情	详情
(VI)	58552	N-[(1S)-1-benzyl-2-({(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}amino)-2-oxoethyl]-2-pyrazinecarboxamide		C₂₉H₃₉BN₄O₄	详情	详情

Extended Information