(2S)-3-hydroxy-2-{[(2S)-2-({[(2S,4R)-4-hydroxypyrrolidinyl]carbonyl}amino)propanoyl]amino}propanoic acid -Drug Synthesis Database

【结构式】

【分子编号】53678

【品名】(2S)-3-hydroxy-2-{[(2S)-2-({[(2S,4R)-4-hydroxypyrrolidinyl]carbonyl}amino)propanoyl]amino}propanoic acid

【CA登记号】n/a

【分子式】C₁₁H₁₉N₃O₆

【分子量】289.28848

【元素组成】C 45.67% H 6.62% N 14.53% O 33.18%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXIV)

The synthesis of the precursor peptide (XVII) was also reported in solution phase. trans-4-Hydroxy-L-proline (XX) was protected as the N-Boc derivative (XII), which was subsequently activated as the pentafluorophenyl ester (XXI). This was condensed with the dipeptide alanyl-serine (XXII) to furnish the protected tripeptide (XXIII). Acidic cleavage of the Boc protecting group of (XXIII) yielded tripeptide (XXIV).

参考文献中间体

合成目标

【1】 Kaufman, M.J.; Almarsson, O.; Nerurkar, M.J.; Lynch, J.E.; Karki, S.B.; Cameron, M.; Lieberman, D.R.; Robbins, M.A.; Shi, Y.-J. (Merck & Co., Inc.); Salt form of a conjugate useful in the treatment of prostate cancer. US 6355611; WO 0130804 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	16094	(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;1-(tert-butoxycarbonyl)-4®-hydroxy-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid	16094	C₁₀H₁₇NO₅	详情	详情
(XX)	14489	(2S,4R)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid; L-Hydroxyproline	51-35-4	C₅H₉NO₃	详情	详情
(XXI)	53675	1-(tert-butyl) 2-(2,3,4,5,6-pentafluorophenyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate	n/a	C₁₆H₁₆F₅NO₅	详情	详情
(XXII)	53676	(2S)-2-{[(2S)-2-aminopropanoyl]amino}-3-hydroxypropanoic acid	n/a	C₆H₁₂N₂O₄	详情	详情
(XXIII)	53677	(2S)-2-{[(2S)-2-({[(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidinyl]carbonyl}amino)propanoyl]amino}-3-hydroxypropanoic acid	n/a	C₁₆H₂₇N₃O₈	详情	详情
(XXIV)	53678	(2S)-3-hydroxy-2-{[(2S)-2-({[(2S,4R)-4-hydroxypyrrolidinyl]carbonyl}amino)propanoyl]amino}propanoic acid	n/a	C₁₁H₁₉N₃O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXIV)

Acylation of 9-fluorenylmethanol (XXV) with glutaric anhydride (XXVI) yielded the glutarate mono-ester (XV). This was further activated as the pentafluorophenyl ester (XXVII) upon treatment with pentafluorophenol and DCC. Coupling of active ester (XXVII) with tripeptide (XXIV) gave rise to the glutaryl tripeptide (XXVIII).

参考文献中间体

合成目标

【1】 Kaufman, M.J.; Almarsson, O.; Nerurkar, M.J.; Lynch, J.E.; Karki, S.B.; Cameron, M.; Lieberman, D.R.; Robbins, M.A.; Shi, Y.-J. (Merck & Co., Inc.); Salt form of a conjugate useful in the treatment of prostate cancer. US 6355611; WO 0130804 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	53680	5-(9H-fluoren-9-ylmethoxy)-5-oxopentanoic acid	n/a	C₁₉H₁₈O₄	详情	详情
(XXIV)	53678	(2S)-3-hydroxy-2-{[(2S)-2-({[(2S,4R)-4-hydroxypyrrolidinyl]carbonyl}amino)propanoyl]amino}propanoic acid	n/a	C₁₁H₁₉N₃O₆	详情	详情
(XXV)	53679	9H-fluoren-9-ylmethanol	24324-17-2	C₁₄H₁₂O	详情	详情
(XXVI)	15512	Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione	108-55-4	C₅H₆O₃	详情	详情
(XXVII)	53681	1-(9H-fluoren-9-ylmethyl) 5-(2,3,4,5,6-pentafluorophenyl) pentanedioate	n/a	C₂₅H₁₇F₅O₄	详情	详情
(XXVIII)	53682	(2S)-2-({(2S)-2-[({(2S,4R)-1-[5-(9H-fluoren-9-ylmethoxy)-5-oxopentanoyl]-4-hydroxypyrrolidinyl}carbonyl)amino]propanoyl}amino)-3-hydroxypropanoic acid	n/a	C₃₀H₃₅N₃O₉	详情	详情

Extended Information