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【结 构 式】

【分子编号】54429

【品名】methyl (E,5S,8S)-8-isobutyl-7,10-dioxo-5-phenethyl-4-{[(3-phenylpropyl)sulfanyl]methyl}-12-(3-pyridinyl)-11-oxa-2,3,6,9-tetraaza-3-dodecen-1-oate

【CA登记号】

【 分 子 式 】C35H45N5O5S

【 分 子 量 】647.839

【元素组成】C 64.89% H 7% N 10.81% O 12.35% S 4.95%

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:(XII)

3(S)-(Allyloxycarbonylamino)-1-chloro-5-phenyl-2-pentanone (VI) is linked to a carbazate resin (VII) to yield the resin-supported compound (VIII) suitable for solid-phase synthesis. The condensation of (VIII) with 3-phenylpropylmercaptan (IX) by means of DIEA in DMF affords the adduct (X), which is deprotected at the allyloxycarbonylamino group by means of Pd(PPh3)4 to provide the amino resin (XI). The condensation of (XI) with the previously described intermediate (V) by means of PyBOP, HOAt and DIEA in DMF gives dipeptide resin (XII). Finally, the cleavage of the target compound from the resin (XII) is performed by means of TFA in trifluoroethanol/water.

1 Ellman, J.A.; Lee, A.; Huang, L. ; Identification of potent and selective mechanism-based inhibitors of the cysteine protease cruzain using solid-phase parallel synthesis. J Med Chem 2002, 45, 3, 676.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 54423 (2S)-4-methyl-2-{[(3-pyridinylmethoxy)carbonyl]amino}pentanoic acid C13H18N2O4 详情 详情
(VI) 54424 allyl (1S)-3-chloro-2-oxo-1-phenethylpropylcarbamate C15H18ClNO3 详情 详情
(VII) 12256 2,4,5-Trifluoro-3-methoxybenzonitrile C8H4F3NO 详情 详情
(VIII) 54425 methyl 2-[(E,2S)-2-{[(allyloxy)carbonyl]amino}-1-(chloromethyl)-4-phenylbutylidene]-1-hydrazinecarboxylate C17H22ClN3O4 详情 详情
(IX) 54426 3-Phenylpropyl mercaptan; 3-Phenyl-1-propanethiol 24734-68-7 C9H12S 详情 详情
(X) 54427 methyl 2-((E,2S)-2-{[(allyloxy)carbonyl]amino}-4-phenyl-1-{[(3-phenylpropyl)sulfanyl]methyl}butylidene)-1-hydrazinecarboxylate C26H33N3O4S 详情 详情
(XI) 54428 methyl 2-((E,2S)-2-amino-4-phenyl-1-{[(3-phenylpropyl)sulfanyl]methyl}butylidene)-1-hydrazinecarboxylate C22H29N3O2S 详情 详情
(XII) 54429 methyl (E,5S,8S)-8-isobutyl-7,10-dioxo-5-phenethyl-4-{[(3-phenylpropyl)sulfanyl]methyl}-12-(3-pyridinyl)-11-oxa-2,3,6,9-tetraaza-3-dodecen-1-oate C35H45N5O5S 详情 详情
Extended Information