(2S)-2-[(anilinocarbothioyl)amino]-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide -Drug Synthesis Database

【结构式】

【分子编号】64227

【品名】(2S)-2-[(anilinocarbothioyl)amino]-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide

【CA登记号】

【分子式】C₁₇H₂₃N₃O₃S

【分子量】349.45404

【元素组成】C 58.43% H 6.63% N 12.02% O 13.74% S 9.18%

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：(VI)

N-Boc-L-Leucine (I) is activated as the corresponding succinimidyl ester (II) upon treatment with N-hydroxysuccinimide and EDC. Coupling of active ester (II) with (S)-alpha-amino-gamma-butyrolactone (III) affords amide (IV). After N-Boc group deprotection of (IV) under acidic conditions, the resultant amine (V) is condensed with phenyl isothiocyanate to furnish thiourea (VI). Finally, reduction of the lactone function of (VI) with DIBAL gives rise to the target cyclic hemiacetal compound.

参考文献中间体

合成目标

【1】 Nakamura, M.; Yamaguchi, M.; Sakai, O.; Inoue, J.; Exploration of cornea permeable calpain inhibitors as anticataract agents. Bioorg Med Chem 2003, 11, 7, 1371.

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)	31819	(2R)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid	16937-99-8	C₁₁H₂₁NO₄	详情	详情
(II)	64224	tert-butyl (1S)-1-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-3-methylbutylcarbamate		C₁₅H₂₄N₂O₆	详情	详情
(III)	64228	(3S)-3-aminodihydro-2(3H)-furanone;L-homoserine lactone;(S)-3-aminodihydrofuran-2(3H)-one		C₄H₇NO₂	详情	详情
(IV)	64225	tert-butyl (1S)-3-methyl-1-({[(3S)-2-oxotetrahydro-3-furanyl]amino}carbonyl)butylcarbamate		C₁₅H₂₆N₂O₅	详情	详情
(V)	64226	(2S)-2-amino-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide		C₁₀H₁₈N₂O₃	详情	详情
(VI)	64227	(2S)-2-[(anilinocarbothioyl)amino]-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide		C₁₇H₂₃N₃O₃S	详情	详情

Extended Information