(2R)-3-(4-methoxy-1H-indol-3-yl)-2-[(2-phenylacetyl)amino]propanoic acid -Drug Synthesis Database

【结构式】

【分子编号】58828

【品名】(2R)-3-(4-methoxy-1H-indol-3-yl)-2-[(2-phenylacetyl)amino]propanoic acid

【CA登记号】

【分子式】C₂₀H₂₀N₂O₄

【分子量】352.38988

【元素组成】C 68.17% H 5.72% N 7.95% O 18.16%

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：(II)

The racemic 4-methoxytryptophan amide (I) is resolved using immobilized Penicillin G acylase, to afford the desired L-aminoacid (III), while leaving unaltered the enantiomeric D-amide (II). After protection of aminoacid (III) as the N-benzyloxycarbonyl derivative (IV), coupling with glycine methyl ester (V) gives dipeptide (VI). Hydrogenolysis of the benzyloxycarbonyl protecting group of (VI) yields amine (VII), which is then coupled with N-Cbz-L-tryptophan (VIII) to produce the protected tripeptide (IX). Hydrogenolysis of (IX) in the presence of Pd/C provides the tripeptide building block (X).

参考文献中间体

合成目标

【1】 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711.

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)	58827	4-methoxy-N-(2-phenylacetyl)tryptophan		C₂₀H₂₀N₂O₄	详情	详情
(II)	58828	(2R)-3-(4-methoxy-1H-indol-3-yl)-2-[(2-phenylacetyl)amino]propanoic acid		C₂₀H₂₀N₂O₄	详情	详情
(III)	58829	(2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid		C₁₂H₁₄N₂O₃	详情	详情
(IV)	58830	(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoic acid		C₂₀H₂₀N₂O₅	详情	详情
(V)	17568	methyl 2-aminoacetate		C₃H₇NO₂	详情	详情
(VI)	58831	methyl 2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate		C₂₃H₂₅N₃O₆	详情	详情
(VII)	58832	methyl 2-{[(2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate		C₁₅H₁₉N₃O₄	详情	详情
(VIII)	18652	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propionic acid	7432-21-5	C₁₉H₁₈N₂O₄	详情	详情
(IX)	58833	methyl (5S,8S)-5-(1H-indol-3-ylmethyl)-8-[(4-methoxy-1H-indol-3-yl)methyl]-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oate		C₃₄H₃₅N₅O₇	详情	详情
(X)	58834	methyl 2-{[(2S)-2-{[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate		C₂₆H₂₉N₅O₅	详情	详情

Extended Information