benzyl (1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】61050

【品名】benzyl (1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethylcarbamate

【CA登记号】

【分子式】C₂₆H₂₆FN₃O₄

【分子量】463.5086632

【元素组成】C 67.37% H 5.65% F 4.1% N 9.07% O 13.81%

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：(V)

In a different strategy, N-Cbz-p-fluorophenylalanine (I) is activated as the mixed anhydride (II) employing isobutyl chloroformate and N-methylmorpholine. Coupling of anhydride (II) with phenylalanine methyl ester (III) leads to the dipeptide ester (IV), which is further treated with methanolic ammonia to produce amide (V). The dipeptide amide (V) is alternatively obtained by direct coupling of mixed anhydride (II) with phenylalanine amide (VI). Hydrogenolysis of the N-Cbz group of (V) in the presence of Pd/C furnishes the deprotected dipeptide (VII).

参考文献中间体

合成目标

【1】 Franzen, H.M.; Bessidskaia, G.; Abedi, V.; Nilsson, A.; Nilsson, M.; Olsson, L.; Frakefamide, an analgesic tetrapeptide: Development of a pilot-plant-scale process. Org Process Res Dev 2002, 6, 6, 788.
【2】 Franzen, H. (AstraZeneca plc); Process for the preparation of a tetrapeptide. WO 9947548 .
【3】 Nilsson, M.; Ellburg, M.; Franzen, H. (AstraZeneca AB); A process for the preparation of H-Tyr-D-Ala-Phe(F)-Phe-NH2. EP 1212350; JP 2003509437; WO 0119849 .

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)	61047	(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-fluorophenyl)propanoic acid		C₁₇H₁₆FNO₄	详情	详情
(II)	61048			C₂₂H₂₄FNO₆	详情	详情
(III)	12324	methyl (2R)-2-amino-3-phenylpropanoate	21685-51-8	C₁₀H₁₃NO₂	详情	详情
(IV)	61049	methyl (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-fluorophenyl)propanoyl]amino}-3-phenylpropanoate		C₂₇H₂₇FN₂O₅	详情	详情
(V)	61050	benzyl (1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethylcarbamate		C₂₆H₂₆FN₃O₄	详情	详情
(VI)	19032	(2S)-2-amino-3-phenylpropanamide	5241-58-7	C₉H₁₂N₂O	详情	详情
(VII)	61044	(2S)-2-amino-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-3-(4-fluorophenyl)propanamide		C₁₈H₂₀FN₃O₂	详情	详情

Extended Information