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

【结构式】

【分子编号】61211

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

【CA登记号】

【分子式】C₂₉H₃₁FN₄O₅

【分子量】534.5875032

【元素组成】C 65.16% H 5.84% F 3.55% N 10.48% O 14.96%

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：(X)

N-Cbz-D-Alanine (VIII) is activated as the mixed anhydride (IX) and subsequently coupled to the dipeptide amide (VII), producing (X). Deprotection of the N-Cbz group of tripeptide (X) by hydrogenolysis over Pd/C yields (XI). The mixed anhydride (XIII) (prepared from N-Cbz-L-tyrosine (XII) and isobutyl chloroformate) is then coupled to tripeptide (XI), producing (XIV). Finally, removal of the N-Cbz group of (XIV) by catalytic hydrogenolysis furnishes the title compound.

参考文献中间体

合成目标

【1】 Franzen, H. (AstraZeneca plc); Process for the preparation of a tetrapeptide. WO 9947548 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	61044	(2S)-2-amino-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-3-(4-fluorophenyl)propanamide	C₁₈H₂₀FN₃O₂	详情	详情
(VIII)	61209	CBZ-L-Alanine; (2S)-2-[[(Benzyloxy)carbonyl]amino]propionic acid; N-((Phenylmethoxy)carbonyl)-alanine; Carbobenzyloxy-L-alanine	C₁₁H₁₃NO₄	详情	详情
(IX)	61210		C₁₆H₂₁NO₆	详情	详情
(X)	61211	benzyl (1R)-2-{[(1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethyl]amino}-1-methyl-2-oxoethylcarbamate	C₂₉H₃₁FN₄O₅	详情	详情
(XI)	61045	(2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-{[(2R)-2-aminopropanoyl]amino}-3-(4-fluorophenyl)propanamide	C₂₁H₂₅FN₄O₃	详情	详情
(XII)	39328	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(4-hydroxyphenyl)propionic acid	C₁₇H₁₇NO₅	详情	详情
(XIII)	61212		C₂₂H₂₅NO₇	详情	详情
(XIV)	61213	(1R)-2-{[(1S)-2-{[(1S)-2-amino-1-benzyl-2-oxoethyl]amino}-1-(4-fluorobenzyl)-2-oxoethyl]amino}-1-methyl-2-oxoethyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate	C₃₈H₃₉FN₄O₈	详情	详情

Extended Information