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【结 构 式】

【分子编号】53389

【品名】3-Phthalimidopropionic acid; Phthalyl-beta-alanine

【CA登记号】3339-73-9

【 分 子 式 】C11H9NO4

【 分 子 量 】219.1968

【元素组成】C 60.28% H 4.14% N 6.39% O 29.2%

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:(I)

Acylation of phenethylamine (III) with acid chloride (II), prepared from phthalimidopropionic acid (I) and SOCl2, gave amide (IV). Subsequent Bischler-Napieralski cyclization of amide (IV) in the presence of POCl3 and P2O5 produced the corresponding dihydroisoquinoline, which was isolated as the hydrochloride salt (V). Catalytic hydrogenation of (V) using PtO2 afforded the tetrahydroisoquinoline (VI). After protection of (VI) as the N-Boc derivative (VII), the primary amine (VIII) was liberated by phthaloyl group hydrazinolysis. Coupling of amine (VIII) with nicotinic acid (IX) employing EDC and HOBt yielded the nicotinamide compound (X). Subsequent acidic cleavage of the Boc protecting group of (X) provided amine (XI), which was finally acylated with 4-butylbenzenesulfonyl chloride (XII) in the presence of resin-bound piperidine to furnish the target sulfonamide.

1 Barn, D.R.; et al.; Parallel synthesis and biological activity of a new class of high affinity and selective delta-opioid ligand. Bioorg Med Chem 2001, 9, 10, 2609.
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) 53389 3-Phthalimidopropionic acid; Phthalyl-beta-alanine 3339-73-9 C11H9NO4 详情 详情
(II) 53390 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride n/a C11H8ClNO3 详情 详情
(III) 18333 Phenethylamine; 2-Phenyl-1-ethanamine 64-04-0 C8H11N 详情 详情
(IV) 53391 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-phenethylpropanamide n/a C19H18N2O3 详情 详情
(V) 53392 2-[2-(3,4-dihydro-1-isoquinolinyl)ethyl]-1H-isoindole-1,3(2H)-dione n/a C19H16N2O2 详情 详情
(VI) 53393 2-[2-(1,2,3,4-tetrahydro-1-isoquinolinyl)ethyl]-1H-isoindole-1,3(2H)-dione n/a C19H18N2O2 详情 详情
(VII) 53394 tert-butyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate n/a C24H26N2O4 详情 详情
(VIII) 53395 tert-butyl 1-(2-aminoethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate n/a C16H24N2O2 详情 详情
(IX) 10752 Nicotinic acid; Niacin 59-67-6 C6H5NO2 详情 详情
(X) 53396 tert-butyl 1-{2-[(3-pyridinylcarbonyl)amino]ethyl}-3,4-dihydro-2(1H)-isoquinolinecarboxylate n/a C22H27N3O3 详情 详情
(XI) 53397 N-[2-(1,2,3,4-tetrahydro-1-isoquinolinyl)ethyl]nicotinamide n/a C17H19N3O 详情 详情
(XII) 53398 4-n-Butylbenzenesulphonyl chloride 54997-92-1 C10H13ClO2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

Treatment of beta-alanine (I) with phthalic anhydride (II) in refluxing toluene provides phthalimidopropionic acid (III), which upon cyclocondensation with 2-aminophenol (IV) in hot polyphosphoric acid provides the benzoxazole derivative (V). Hydrazinolysis of phthalimide (V) affords the primary amine (VI), which is finally condensed with pyrazole-1-carboxamidine hydrochloride (VII) in DMF to produce the target guanidine compound.

1 López-Tudanca, P.; Labeaga, L.; Innerárity, A.; Alonso-Cires, L.; Tapia, I.; Mosquera, R.; Orjales, A.; Synthesis and pharmacological characterization of a new benzoxazole derivative as a potent 5-HT3 receptor agonist. Bioorg Med Chem 2003, 11, 13, 2709.
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) 17022 beta-Alanine; 3-aminopropionic acid 107-95-9 C3H7NO2 详情 详情
(II) 11900 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride 85-44-9 C8H4O3 详情 详情
(III) 53389 3-Phthalimidopropionic acid; Phthalyl-beta-alanine 3339-73-9 C11H9NO4 详情 详情
(IV) 18663 o-aminophenol; 2-aminophenol 95-55-6 C6H7NO 详情 详情
(V) 64846 2-[2-(1,3-benzoxazol-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione C17H12N2O3 详情 详情
(VI) 64847 2-(1,3-benzoxazol-2-yl)-1-ethanamine; 2-(1,3-benzoxazol-2-yl)ethylamine C9H10N2O 详情 详情
(VII) 15983 1H-pyrazole-1-carboximidamide 4023-00-1 C4H6N4 详情 详情
Extended Information