N-[(2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-nitrobenzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】45532

【品名】N-[(2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-nitrobenzenesulfonamide

【CA登记号】

【分子式】C₃₄H₃₉N₃O₅S

【分子量】601.76688

【元素组成】C 67.86% H 6.53% N 6.98% O 13.29% S 5.33%

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：(IX)

The reaction of N,N-dibenzyl-L-alaninal (I) with nitromethane, catalyzed by the chiral ammonium salt (II) and KF in THF gives the chiral nitroalcohol (III), which is reduced with NiCl2 and NaBH4 to yield the aminoalcohol (IV). The condensation of (IV) with isobutyraldehyde (V) affords the Schiff base (VI), which is reduced with NaBH4 to provide the secondary amine (VII). The reaction of (VII) with 4-nitrobenzenesulfonyl chloride (VIII) and TEA in dichloromethane furnishes the sulfonamide (IX), which is deprotected by hydrogenation with H2 over Pd/C in methanol, giving the diamino compound (X). Finally, this compound is condensed with 3(S)-tetrahydrofuryl (N-oxysuccinimidyl) carbonate (XI) by means of TEA in dichloromethane to afford the target carbamate.

参考文献中间体

合成目标

【1】 Corey, E.J.; Zhang, F.-Y.; Re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478). Angew Chem. Int Ed Engl 1999, 38, 13-14, 1931.

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)	37936	(2S)-2-(dibenzylamino)-3-phenylpropanal		C₂₃H₂₃NO	详情	详情
(II)	45528	1-(9-anthrylmethyl)-2-[(benzyloxy)(4-quinolinyl)methyl]-5-vinyl-1-azoniabicyclo[2.2.2]octane fluoride		C₄₁H₃₉FN₂O	详情	详情
(III)	45529	(2R,3S)-3-(dibenzylamino)-1-nitro-4-phenyl-2-butanol		C₂₄H₂₆N₂O₃	详情	详情
(IV)	45530	(2R,3S)-1-amino-3-(dibenzylamino)-4-phenyl-2-butanol		C₂₄H₂₈N₂O	详情	详情
(V)	13226	2-Methylpropanal; Isobutyraldehyde	78-84-2	C₄H₈O	详情	详情
(VI)	45531	(2R,3S)-3-(dibenzylamino)-1-[[(E)-2-methylpropylidene]amino]-4-phenyl-2-butanol		C₂₈H₃₄N₂O	详情	详情
(VII)	37940	(2R,3S)-3-(dibenzylamino)-1-(isobutylamino)-4-phenyl-2-butanol		C₂₈H₃₆N₂O	详情	详情
(VIII)	15809	4-nitrobenzenesulfonyl chloride	98-74-8	C₆H₄ClNO₄S	详情	详情
(IX)	45532	N-[(2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-nitrobenzenesulfonamide		C₃₄H₃₉N₃O₅S	详情	详情
(X)	45533	4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-isobutylbenzenesulfonamide		C₂₀H₂₉N₃O₃S	详情	详情
(XI)	39664	1-([[(3S)tetrahydro-3-furanyloxy]carbonyl]oxy)-2,5-pyrrolidinedione		C₉H₁₁NO₆	详情	详情

Extended Information