benzyl (1R)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(2-naphthylmethyl)-2-oxoethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】54460

【品名】benzyl (1R)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(2-naphthylmethyl)-2-oxoethylcarbamate

【CA登记号】

【分子式】C₂₉H₃₅N₃O₆

【分子量】521.61352

【元素组成】C 66.78% H 6.76% N 8.06% O 18.4%

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)

The monoamine intermediate (IV) has been obtained as follows: The condensation of 2(R)-(benzyloxycarbonylamino)-3-(2-naphthyl)propionic acid (I) with 3-(tert-butoxycarbonylamino)-2-hydroxypropylamine (II) gives the corresponding amide (III), which is regioselectively deprotected by hydrogenolysis to yield the desired monoamine (IV). The condensation of 2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one (V) with 4-chlorobutyric acid ethyl ester (VI) gives the corresponding cyclic amide (VII), which is hydrolyzed to afford the carboxylic acid (VIII). The condensation of acid (VIII) with the intermediate amine (IV) provides the amide (IX), which is finally N-deprotected to furnish the target diamide.

参考文献中间体

合成目标

【1】 Huang, P.; Funamizu, H.; Loew, G.H.; et al.; Rational design, discovery, and synthesis of a novel series of potent growth hormone secretagogues. J Med Chem 2001, 44, 24, 4082.
【2】 Salmon, R.; Sunley, R.L.; Godfrey, C.R.A.; Urch, C.J.; Lewis, T.; Bishop, N.D. (AstraZeneca plc); Bicycle amine derivs.. US 5912254; US 6066646 .

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)	54458	(2R)-2-{[(benzyloxy)carbonyl]amino}-3-(2-naphthyl)propanoic acid		C₂₁H₁₉NO₄	详情	详情
(II)	54459	tert-butyl 3-amino-2-hydroxypropylcarbamate		C₈H₁₈N₂O₃	详情	详情
(III)	54460	benzyl (1R)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(2-naphthylmethyl)-2-oxoethylcarbamate		C₂₉H₃₅N₃O₆	详情	详情
(IV)	54461	tert-butyl 3-{[(2R)-2-amino-3-(2-naphthyl)propanoyl]amino}-2-hydroxypropylcarbamate		C₂₁H₂₉N₃O₄	详情	详情
(V)	48910	2,3,4,5-Tetrahydro-1,5-benzothiazepin-4-one		C₉H₉NOS	详情	详情
(VI)	54462	4-Chlorobutyric acid ethyl ester; Ethyl 4-chlorobutyrate	3153-36-4	C₆H₁₁ClO₂	详情	详情
(VII)	54463	ethyl 4-[4-oxo-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]butanoate		C₁₅H₁₉NO₃S	详情	详情
(VIII)	54464	4-[4-oxo-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]butanoic acid		C₁₃H₁₅NO₃S	详情	详情
(IX)	54465	tert-butyl 2-hydroxy-3-{[(2R)-3-(2-naphthyl)-2-({4-[4-oxo-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]butanoyl}amino)propanoyl]amino}propylcarbamate		C₃₄H₄₂N₄O₆S	详情	详情

Extended Information