tert-butyl propyl[4-([[4-(trifluoromethoxy)phenyl]sulfonyl]amino)phenethyl]carbamate -Drug Synthesis Database

【结构式】

【分子编号】47988

【品名】tert-butyl propyl[4-([[4-(trifluoromethoxy)phenyl]sulfonyl]amino)phenethyl]carbamate

【CA登记号】

【分子式】C₂₃H₂₉F₃N₂O₅S

【分子量】502.5549496

【元素组成】C 54.97% H 5.82% F 11.34% N 5.57% O 15.92% S 6.38%

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：(VII)

4-Nitrophenethylamine (I) was acylated with propionyl chloride and the resulting amide (II) was reduced to amine (III) with borane-dimethyl sulfide complex in refluxing THF. Amine (III) was then protected as the tert-butyl carbamate (IV) using Boc2O in THF. Subsequent catalytic hydrogenation of the nitro group of (IV) over Pd/C furnished aniline (V), which was coupled with 4-(trifluoromethoxy)benzenesulfonyl chloride (VI) to yield sulfonamide (VII). The Boc protecting group of (VII) was finally removed by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Romero, A.G.; Leiby, J.A. (Pharmacia Corp.); Phenylsulfonamide-phenylethylamines useful as dopamine receptors. EP 1077935; WO 9958499 .

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)	26560	4-nitrophenethylamine	24954-67-4	C₈H₁₀N₂O₂	详情	详情
(II)	47983	N-(4-nitrophenethyl)propanamide		C₁₁H₁₄N₂O₃	详情	详情
(III)	47984	N-(4-nitrophenethyl)-1-propanamine; N-(4-nitrophenethyl)-N-propylamine		C₁₁H₁₆N₂O₂	详情	详情
(IV)	47985	tert-butyl 4-nitrophenethyl(propyl)carbamate		C₁₆H₂₄N₂O₄	详情	详情
(V)	47986	tert-butyl 4-aminophenethyl(propyl)carbamate		C₁₆H₂₆N₂O₂	详情	详情
(VI)	47987	4-(trifluoromethoxy)benzenesulfonyl chloride	94108-56-2	C₇H₄ClF₃O₃S	详情	详情
(VII)	47988	tert-butyl propyl[4-([[4-(trifluoromethoxy)phenyl]sulfonyl]amino)phenethyl]carbamate		C₂₃H₂₉F₃N₂O₅S	详情	详情

Extended Information