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【结 构 式】

【分子编号】37258

【品名】2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetic acid

【CA登记号】

【 分 子 式 】C18H21N5O6S

【 分 子 量 】435.46084

【元素组成】C 49.65% H 4.86% N 16.08% O 22.04% S 7.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XI)

Nalpha-(Benzyloxycarbonyl)-1,4-diaminobutyric acid (I) was protected as the Nomega-Boc derivative (II) and then coupled to glycine ethyl ester (III) by means of EDC and HOBt to produce dipeptide (IV). Hydrogenolysis of the benzyloxycarbonyl group of (IV) to give (V), followed by condensation with alpha-toluenesulfonyl chloride (VI) gave sulfonamide (VII). Side-chain deprotection of (VII) with HCl liberated amine (VIII), which was acylated with 2-pyrazinecarboxylic acid (IX) to afford amide (X). Saponification of the ethyl ester of (X) with LiOH gave carboxylic acid (XI).

1 Ho, J.Z.; et al.; Exploration solid-phase synthesis of factor Xa inhibitors: Discovery and application of P3-heterocyclic amides as novel types of non-basic arginine surrogates. Bioorg Med Chem Lett 1999, 9, 24, 3459.
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) 37250 (2R)-4-amino-2-[[(benzyloxy)carbonyl]amino]butyric acid 62234-40-6 C12H16N2O4 详情 详情
(II) 37251 (2R)-2-[[(benzyloxy)carbonyl]amino]-4-[(tert-butoxycarbonyl)amino]butyric acid C17H24N2O6 详情 详情
(III) 10309 ethyl 2-aminoacetate; Glycine ethyl ester 459-73-4 C4H9NO2 详情 详情
(IV) 37252 ethyl 2-([(2R)-2-[[(benzyloxy)carbonyl]amino]-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate C21H31N3O7 详情 详情
(V) 37253 ethyl 2-([(2R)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate C13H25N3O5 详情 详情
(VI) 25151 phenylmethanesulfonyl chloride 1939-99-7 C7H7ClO2S 详情 详情
(VII) 37254 ethyl 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate C20H31N3O7S 详情 详情
(VIII) 37255 ethyl 2-([(2R)-4-amino-2-[(benzylsulfonyl)amino]butanoyl]amino)acetate C15H23N3O5S 详情 详情
(IX) 37256 2-pyrazinecarboxylic acid; Pyrazinoic acid 98-97-5 C5H4N2O2 详情 详情
(X) 37257 ethyl 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetate C20H25N5O6S 详情 详情
(XI) 37258 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetic acid C18H21N5O6S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XI)

The carboxylic acid (XI) was coupled with Ngamma-Pmc-argininol (XII) giving (XIII). Deprotection of the Pmc group of (XIII) with trifluoroacetic acid provided the free guanidine (XIV). Finally, Swern oxidation of the primary alcohol of (XIV) with concomitant cyclization of the resulting aldehyde furnished the title compound.

1 Ho, J.Z.; et al.; Exploration solid-phase synthesis of factor Xa inhibitors: Discovery and application of P3-heterocyclic amides as novel types of non-basic arginine surrogates. Bioorg Med Chem Lett 1999, 9, 24, 3459.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 37258 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetic acid C18H21N5O6S 详情 详情
(XII) 37259 N-((E)-amino[[(4S)-4-amino-5-hydroxypentyl]amino]methylidene)-2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromene-6-sulfonamide C20H36N4O4S 详情 详情
(XIII) 37260 N-[(3R)-4-[(2-[[(1S)-4-[(amino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]imino]methyl)amino]-1-(hydroxymethyl)butyl]amino]-2-oxoethyl)amino]-3-[(benzylsulfonyl)amino]-4-oxobutyl]-2-pyrazinecarboxamide C38H55N9O9S2 详情 详情
(XIV) 37261 N-[(3R)-4-[(2-[[(1S)-4-[[amino(imino)methyl]amino]-1-(hydroxymethyl)butyl]amino]-2-oxoethyl)amino]-3-[(benzylsulfonyl)amino]-4-oxobutyl]-2-pyrazinecarboxamide C24H35N9O6S 详情 详情
Extended Information