ethyl 3-({2-[(3,3,3-triphenylpropanoyl)amino]acetyl}amino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】57641

【品名】ethyl 3-({2-[(3,3,3-triphenylpropanoyl)amino]acetyl}amino)propanoate

【CA登记号】

【分子式】C₂₈H₃₀N₂O₄

【分子量】458.55728

【元素组成】C 73.34% H 6.59% N 6.11% O 13.96%

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：(VI)

Coupling between ethyl 3-aminopropionate (I) and N-Boc-glycine (II) by means of EDC and HOBt affords the protected dipeptide (III). After acidic Boc group cleavage in (III), the N-deprotected dipeptide (IV) is acylated by 3,3,3-triphenylpropionic acid (V) to produce amide (VI). Saponification of the ethyl ester group of (VI) yields acid (VII). This is coupled with (R)-1-Boc-3-(aminomethyl)piperidine (VIII) to afford amide (IX), which is further subjected to acidic N-Boc group cleavage. The resultant piperidine derivative (X) is then reductively condensed with cyclohexanecarboxaldehyde (XI) in the presence of NaBH(OAc)3 to furnish the title compound.

参考文献中间体

合成目标

【1】 Kimura, T.; Noguchi, K.; Otake, N.; Uchiyama, M.; Naya, A.; Sagara, Y.; Numazawa, T.; Fujikawa, T. (Banyu Pharmaceutical Co., Ltd.); Novel amide derivs.. EP 1213281; WO 0107406 .

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)	17639	beta-Alanine, ethyl ester; ethyl 3-aminopropanoate	924-73-2	C₅H₁₁NO₂	详情	详情
(II)	18066	N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid	4530-20-5	C₇H₁₃NO₄	详情	详情
(III)	57638	ethyl 3-({2-[(tert-butoxycarbonyl)amino]acetyl}amino)propanoate		C₁₂H₂₂N₂O₅	详情	详情
(IV)	57639	ethyl 3-[(2-aminoacetyl)amino]propanoate		C₇H₁₄N₂O₃	详情	详情
(V)	57640	3,3,3-Triphenylpropionic acid; Tritylacetic acid	900-91-4	C₂₁H₁₈O₂	详情	详情
(VI)	57641	ethyl 3-({2-[(3,3,3-triphenylpropanoyl)amino]acetyl}amino)propanoate		C₂₈H₃₀N₂O₄	详情	详情
(VII)	57642	N-{2-[(3,3,3-triphenylpropanoyl)amino]acetyl}-beta-alanine		C₂₆H₂₆N₂O₄	详情	详情
(VIII)	57643	tert-butyl (3R)-3-(aminomethyl)-1-piperidinecarboxylate		C₁₁H₂₂N₂O₂	详情	详情
(IX)	57644	tert-butyl (3R)-3-({[3-({2-[(3,3,3-triphenylpropanoyl)amino]acetyl}amino)propanoyl]amino}methyl)-1-piperidinecarboxylate		C₃₇H₄₆N₄O₅	详情	详情
(X)	57645	N-{2-oxo-2-[(3-oxo-3-{[(3S)piperidinylmethyl]amino}propyl)amino]ethyl}-3,3,3-triphenylpropanamide		C₃₂H₃₈N₄O₃	详情	详情
(XI)	33694	cyclohexanecarbaldehyde	2043-61-0	C₇H₁₂O	详情	详情

Extended Information