S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec- -Drug Synthesis Database

【结构式】

【分子编号】31376

【品名】S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-

【CA登记号】

【分子式】C₆₄H₇₃ClN₁₀O₁₀S

【分子量】1209.86372

【元素组成】C 63.54% H 6.08% Cl 2.93% N 11.58% O 13.22% S 2.65%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(XIV)

Compound (X) was subsequently submitted to further coupling and deprotection cycles with the protected amino acids N-Boc-D-tryptophan (XI) and N-Boc-L-(3-pyridyl)alanine (XIII) to afford the peptide-resins (XII) and (XIV), respectively.

参考文献中间体

合成目标

【1】 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
【2】 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	31375	S-[(2R,5S,8S)-8-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate		C₄₅H₅₅ClN₆O₈S	详情	详情
(XI)	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
(XII)	31377	S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate		C₅₆H₆₅ClN₈O₉S	详情	详情
(XIII)	31378	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-pyridinyl)propionic acid		C₁₃H₁₈N₂O₄	详情	详情
(XIV)	31376	S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-		C₆₄H₇₃ClN₁₀O₁₀S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

Compound (XIV) was subsequently submitted to further coupling and deprotection cycles with the protected amino acids N-Boc-S-(4-methylbenzyloxycarbonyl)-D-cysteine (XV) and N-Boc-L-(4-chlorophenyl)- alanine (XVII) to afford the peptide-resins (XVI) and (XVIII), respectively.

参考文献中间体

合成目标

【1】 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
【2】 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	31376	S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-		C₆₄H₇₃ClN₁₀O₁₀S	详情	详情
(XV)	31382	(2S)-2-[(tert-butoxycarbonyl)amino]-3-([[(4-methylbenzyl)oxy]carbonyl]sulfanyl)propionic acid		C₁₇H₂₃NO₆S	详情	详情
(XVI)	31379	S-[(2R,5S,8S,11R,14S,17S)-17-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-8-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-11-(1H-indol-3-ylmethyl)-22-(4-methylphenyl)-4,7,10,13,16,20-hexaoxo-14-(3-pyridiny		C₇₆H₈₆ClN₁₁O₁₃S₂	详情	详情
(XVII)	31381	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propionic acid	68090-88-0	C₁₄H₁₈ClNO₄	详情	详情
(XVIII)	31380	S-[(2S,5S,8R,11S,14S,17R)-17-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoyl]amino]-14-(tert-butyl)-11-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-8-(1H-indol-3-		C₉₀H₁₀₂Cl₂N₁₂O₁₆S₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XIII)

The coupling and deprotection cycles was continued with N-Boc-L-(3-pyridyl)alanine (XII), N-Boc-S-(4-methylbenzyloxy-carbonyl)-D-cysteine (IV), and N-Boc-L-4-fluorophenylalanine (XV), yielding the peptide resins (XIII), (XIV) and (XVI), respectively.

参考文献中间体

合成目标

【1】 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
【2】 Rossowski, W.J.; Cheng, B.-L.; Jiang, N.-Y.; Coy, D.-H.; Examination of somatostatin involvement in the inhibitory action of GIP, GLP-1, amylin and adrenomedullin on gastric acid release using a new SRIF antagonist analogue. Br J Pharmacol 1998, 125, 1081.
【3】 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	31371	(2R)-2-[(tert-butoxycarbonyl)amino]-3-([[(4-methylbenzyl)oxy]carbonyl]sulfanyl)propionic acid	C₁₇H₂₃NO₆S	详情	详情
(XI)	31377	S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate	C₅₆H₆₅ClN₈O₉S	详情	详情
(XII)	34944	(2S)-2-[(tert-butoxycarbonyl)(3-pyridinyl)amino]propionic acid	C₁₃H₁₈N₂O₄	详情	详情
(XIII)	31376	S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-	C₆₄H₇₃ClN₁₀O₁₀S	详情	详情
(XIV)	31379	S-[(2R,5S,8S,11R,14S,17S)-17-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-8-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-11-(1H-indol-3-ylmethyl)-22-(4-methylphenyl)-4,7,10,13,16,20-hexaoxo-14-(3-pyridiny	C₇₆H₈₆ClN₁₁O₁₃S₂	详情	详情
(XV)	25929	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-fluorophenyl)propionic acid	C₁₄H₁₈FNO₄	详情	详情
(XVI)	34945		C₉₀H₁₀₂ClFN₁₂O₁₆S₂	详情	详情

Extended Information