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【结 构 式】

【分子编号】54464

【品名】4-[4-oxo-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]butanoic acid

【CA登记号】

【 分 子 式 】C13H15NO3S

【 分 子 量 】265.33304

【元素组成】C 58.85% H 5.7% N 5.28% O 18.09% S 12.09%

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:(VIII)

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.

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