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

【结构式】

【分子编号】61215

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

【CA登记号】

【分子式】C₂₀H₂₂N₂O₆

【分子量】386.40456

【元素组成】C 62.17% H 5.74% N 7.25% O 24.84%

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)

In an alternative procedure, N-Cbz-L-tyrosine (I) is condensed with D-alanine methyl ester (II), either employing TBTU as the coupling reagent or via previous activation as the mixed anhydride with isobutyl chloroformate, to produce dipeptide (III). After alkaline hydrolysis of the methyl ester function of (III), the resultant carboxylic acid (IV) is coupled to dipeptide amide (V) yielding the protected tetrapeptide (VI). Finally, deprotection of (VI) is carried out by catalytic hydrogenolysis over Pd/C.

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】 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	分子式	供应商	用于合成
(I)	39328	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(4-hydroxyphenyl)propionic acid	C₁₇H₁₇NO₅	详情	详情
(II)	20694	methyl (2S)-2-aminopropanoate	C₄H₉NO₂	详情	详情
(III)	61214	methyl (2R)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}propanoate	C₂₁H₂₄N₂O₆	详情	详情
(IV)	61215	(2R)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}propanoic acid	C₂₀H₂₂N₂O₆	详情	详情
(V)	61044	(2S)-2-amino-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-3-(4-fluorophenyl)propanamide	C₁₈H₂₀FN₃O₂	详情	详情
(VI)	61216	benzyl (1S)-2-[((1R)-2-{[(1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethyl]amino}-1-methyl-2-oxoethyl)amino]-1-(4-hydroxybenzyl)-2-oxoethylcarbamate	C₃₈H₄₀FN₅O₇	详情	详情

Extended Information