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【结 构 式】

【分子编号】51362

【品名】2-allyl 1,8-dibenzyl (2S,3aS,8aS)-2-[(dimethylamino)methyl]-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

【CA登记号】

【 分 子 式 】C33H35N3O6

【 分 子 量 】569.65752

【元素组成】C 69.58% H 6.19% N 7.38% O 16.85%

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)

Esterification of N-benzyloxycarbonyl-(R)-tryptophan (I) with allyl alcohol (II) using DCC gave ester (III). The cyclization of (III) to afford diastereoselectively the pyrroloindole derivative (IV) was achieved in trifluoroacetic acid as the solvent. A second N-benzyloxycarbonyl protecting group was then introduced at the indoline nitrogen of (IV), yielding (V). Mannich reaction of the lithium anion of (V) with Eschenmoser's salt provided the (dimethylamino)methyl compound (VI). Ring opening of (VI) to the indole (VII) was performed with sulfuric acid in aqueous methanol. The allyl ester of (VII) was then removed by means of morpholine and palladium catalyst to produce acid (VIII), which was coupled with (S)-alpha-methylbenzylamine (IX) to give amide (X). After hydrogenolysis of the two benzyloxycarbonyl protecting groups of (X), the free amine (XI) was acylated with 2-benzofuranylmethyl chloroformate to furnish the title carbamate.

1 Ashwood, V.A.; et al.; Utilization of an intramolecular hydrogen bond to increase the CNS penetration of an NK1 receptor antagonist. J Med Chem 2001, 44, 14, 2276.
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) 18652 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propionic acid 7432-21-5 C19H18N2O4 详情 详情
(II) 12234 2-Propen-1-ol; Allyl alcohol 107-18-6 C3H6O 详情 详情
(III) 51359 allyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propanoate C22H22N2O4 详情 详情
(IV) 51360 2-allyl 1-benzyl (2R,3aS,8aS)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1,2(2H)-dicarboxylate C22H22N2O4 详情 详情
(V) 51361 2-allyl 1,8-dibenzyl (2R,3aS,8aR)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate C30H28N2O6 详情 详情
(VI) 51362 2-allyl 1,8-dibenzyl (2S,3aS,8aS)-2-[(dimethylamino)methyl]-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate C33H35N3O6 详情 详情
(VII) 51363 benzyl 3-[(2S)-3-(allyloxy)-2-[[(benzyloxy)carbonyl]amino]-2-[(dimethylamino)methyl]-3-oxopropyl]-1H-indole-1-carboxylate C33H35N3O6 详情 详情
(VIII) 51364 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[1-[(benzyloxy)carbonyl]-1H-indol-3-yl]-2-[(dimethylamino)methyl]propionic acid C30H31N3O6 详情 详情
(IX) 20042 (1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine C8H11N 详情 详情
(X) 51365 benzyl 3-((2S)-2-[[(benzyloxy)carbonyl]amino]-2-[(dimethylamino)methyl]-3-oxo-3-[[(1S)-1-phenylethyl]amino]propyl)-1H-indole-1-carboxylate C38H40N4O5 详情 详情
(XI) 51367 (2S)-2-amino-3-(dimethylamino)-2-(1H-indol-3-ylmethyl)-N-[(1S)-1-phenylethyl]propanamide C22H28N4O 详情 详情
(XII) 51366 2-[[(chlorocarbonyl)oxy]methyl]-1-benzofuran C10H7ClO3 详情 详情
Extended Information