N-[(2R)-2-(methylamino)-3-phenylpropyl]methanesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】25305

【品名】N-[(2R)-2-(methylamino)-3-phenylpropyl]methanesulfonamide

【CA登记号】

【分子式】C₁₁H₁₈N₂O₂S

【分子量】242.3422

【元素组成】C 54.52% H 7.49% N 11.56% O 13.2% S 13.23%

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：(VI)

N-Boc-N-Methyl-D-phenylalaninol (I) was oxidized to aldehyde (II) using SO3-pyridine complex. Reductive amination of (II) with benzylamine to yield (III), followed by hydrogenolytic debenzylation then furnished the monoprotected diamine (IV). This was condensed with methanesulfonyl chloride to yield sulfonamide (V). After deprotection of the Boc group of (V) with trifluoroacetic acid, amine (VI) was coupled with N-Boc-N-methyl-D-naphthylalanine (VII) using EDC and HOAt. The resulting amide (VIII) was further deprotected with trifluoroacetic acid, and then coupled with 5-(tert-butoxycarbonyl)amino-5-methyl-2-hexenoic acid (IX) to yield (X). Finally, acid deprotection of the Boc group of (X) furnished the target compound.

参考文献中间体

合成目标

【1】 Hansen, B.S.; Peschke, B.; New growth hormone secretagogues: C-terminal modified sulfonamide-analogues of NN703. Bioorg Med Chem Lett 1999, 9, 9, 1295.

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)	25300	tert-butyl (1R)-1-benzyl-2-hydroxyethyl(methyl)carbamate		C₁₅H₂₃NO₃	详情	详情
(II)	25301	tert-butyl (1R)-1-benzyl-2-oxoethyl(methyl)carbamate		C₁₅H₂₁NO₃	详情	详情
(III)	25302	tert-butyl (1R)-1-benzyl-2-(benzylamino)ethyl(methyl)carbamate		C₂₂H₃₀N₂O₂	详情	详情
(IV)	25303	tert-butyl (1R)-2-amino-1-benzylethyl(methyl)carbamate		C₁₅H₂₄N₂O₂	详情	详情
(V)	25304	tert-butyl (1R)-1-benzyl-2-[(methylsulfonyl)amino]ethyl(methyl)carbamate		C₁₆H₂₆N₂O₄S	详情	详情
(VI)	25305	N-[(2R)-2-(methylamino)-3-phenylpropyl]methanesulfonamide		C₁₁H₁₈N₂O₂S	详情	详情
(VII)	22189	(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-(2-naphthyl)propionic acid	147577-61-5	C₁₉H₂₃NO₄	详情	详情
(VIII)	25306	tert-butyl (1R)-2-[[(1R)-1-benzyl-2-[(methylsulfonyl)amino]ethyl](methyl)amino]-1-(2-naphthylmethyl)-2-oxoethyl(methyl)carbamate		C₃₀H₃₉N₃O₅S	详情	详情
(IX)	22191	(E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid		C₁₂H₂₁NO₄	详情	详情
(X)	25307	tert-butyl (E,7R,10R)-10-benzyl-1,1,6,9-tetramethyl-7-(2-naphthylmethyl)-5,8,13,13-tetraoxo-13lambda(6)-thia-6,9,12-triaza-3-tetradecen-1-ylcarbamate		C₃₇H₅₀N₄O₆S	详情	详情

Extended Information