tert-butyl (1S)-2,2-dimethyl-1-(2,4,5-trifluorobenzoyl)propylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】64475

【品名】tert-butyl (1S)-2,2-dimethyl-1-(2,4,5-trifluorobenzoyl)propylcarbamate

【CA登记号】

【分子式】C₁₇H₂₂F₃NO₃

【分子量】345.3618296

【元素组成】C 59.12% H 6.42% F 16.5% N 4.06% O 13.9%

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：(III)

Condensation of N-Boc-tert-leucine pentafluorophenyl ester (I) with Grignard reagent (II) furnishes the trifluorophenyl ketone (III). After acidic N-Boc group cleavage in (III), the resultant amine (IV) is coupled with the N-formyl-N-(benzyloxy)aminoacid (V) to provide the corresponding amide (VI). Displacement of the 4-fluoro group of (VI) with morpholine (VII) gives rise to the morpholinophenyl ketone (VIII). The O-benzyl protecting group of (VIII) is finally removed by transfer hydrogenolysis in the presence of cyclohexene and Pd/C to afford the target hydroxylamine compound (1).

参考文献中间体

合成目标

【1】 Ayscough, A.; Beckett, R.P.; Brookings, D.C.; Clements, J.M.; East, S.P.; Keavey, K.; Smith, K.H.; Thomas, W.; Thompson, A.J.; Todd, R.S.; A new series of potent PDF inhibitors displaying broad-spectrum antibacterial activity against respiratory tract infections. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1677.

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)	60284	2,3,4,5,6-pentafluorophenyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3,3-dimethylbutanoate		C₁₇H₂₀F₅NO₄	详情	详情
(II)	64474	bromo(2,4,5-trifluorophenyl)magnesium		C₆H₂BrF₃Mg	详情	详情
(III)	64475	tert-butyl (1S)-2,2-dimethyl-1-(2,4,5-trifluorobenzoyl)propylcarbamate		C₁₇H₂₂F₃NO₃	详情	详情
(IV)	64476	(2S)-2-amino-3,3-dimethyl-1-(2,4,5-trifluorophenyl)-1-butanone		C₁₂H₁₄F₃NO	详情	详情
(V)	64477	(2R)-3-[(benzyloxy)(formyl)amino]-2-(cyclopentylmethyl)propanoic acid		C₁₇H₂₃NO₄	详情	详情
(VI)	64478	(2R)-3-[(benzyloxy)(formyl)amino]-2-(cyclopentylmethyl)-N-[(1S)-2,2-dimethyl-1-(2,4,5-trifluorobenzoyl)propyl]propanamide		C₂₉H₃₅F₃N₂O₄	详情	详情
(VII)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(VIII)	64479	(2R)-3-[(benzyloxy)(formyl)amino]-2-(cyclopentylmethyl)-N-{(1S)-1-[2,5-difluoro-4-(4-morpholinyl)benzoyl]-2,2-dimethylpropyl}propanamide		C₃₃H₄₃F₂N₃O₅	详情	详情

Extended Information