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【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.

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