(E)-5-[(tert-butoxycarbonyl)(methyl)amino]-5-methyl-2-hexenoic acid -Drug Synthesis Database

【结构式】

【分子编号】37820

【品名】(E)-5-[(tert-butoxycarbonyl)(methyl)amino]-5-methyl-2-hexenoic acid

【CA登记号】

【分子式】C₁₃H₂₃NO₄

【分子量】257.32996

【元素组成】C 60.68% H 9.01% N 5.44% O 24.87%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

Reduction of N-Boc-3-amino-3-methylbutanoic acid (I) to alcohol (II) was achieved via formation of the corresponding mixed anhydride with ethyl chloroformate, followed by treatment with LiBH4. Swern oxidation then produced aldehyde (III), which was subjected to a Horner-Emmons condensation with triethyl phosphonoacetate (IV) to afford unsaturated ester (V). Ester hydrolysis with LiOH yielded carboxylic acid (VI). Subsequent alkylation of (VI) with methyl iodide and NaH furnished de N-methyl derivative (VII).

参考文献中间体

合成目标

【1】 Madsen, K.; Kruse hansen, T.; Watson, B.; Peschke, B.; Langeland Johansen, N.; Sehested Hansen, B.; Lau, J.; Thogersen, H.; Ankersen, M.; Petersen, H.; Synthesis and in vitro characterization of new growth hormone secretagogues derived form ipamorelin with dipeptidomimetic N-terminals. Eur J Med Chem 1999, 34, 5, 363.
【2】 Hansen, T.K.; Peschke, B.; Lau, J.; Lundt, B.F.; Ankersen, M.; Watson, B.; Madsen, K. (Novo Nordisk A/S); Cpds. with growth hormone releasing properties. JP 1999209336; JP 1999501054; JP 2000143613; US 6127391; WO 9723508 .

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)	22193	3-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid		C₁₀H₁₉NO₄	详情	详情
(II)	22194	tert-butyl 3-hydroxy-1,1-dimethylpropylcarbamate		C₁₀H₂₁NO₃	详情	详情
(III)	22195	tert-butyl 1,1-dimethyl-3-oxopropylcarbamate		C₁₀H₁₉NO₃	详情	详情
(IV)	10019	Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate	867-13-0	C₈H₁₇O₅P	详情	详情
(V)	27230	ethyl (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoate		C₁₄H₂₅NO₄	详情	详情
(VI)	22191	(E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid		C₁₂H₂₁NO₄	详情	详情
(VII)	37820	(E)-5-[(tert-butoxycarbonyl)(methyl)amino]-5-methyl-2-hexenoic acid		C₁₃H₂₃NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

Coupling of amino acid (VII) with dipeptide (XIII) employing EDC and HOAt yielded tripeptide (XIV). The Boc group of (XIV) was then deprotected with trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Madsen, K.; Kruse hansen, T.; Watson, B.; Peschke, B.; Langeland Johansen, N.; Sehested Hansen, B.; Lau, J.; Thogersen, H.; Ankersen, M.; Petersen, H.; Synthesis and in vitro characterization of new growth hormone secretagogues derived form ipamorelin with dipeptidomimetic N-terminals. Eur J Med Chem 1999, 34, 5, 363.
【2】 Hansen, T.K.; Peschke, B.; Lau, J.; Lundt, B.F.; Ankersen, M.; Watson, B.; Madsen, K. (Novo Nordisk A/S); Cpds. with growth hormone releasing properties. JP 1999209336; JP 1999501054; JP 2000143613; US 6127391; WO 9723508 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	37820	(E)-5-[(tert-butoxycarbonyl)(methyl)amino]-5-methyl-2-hexenoic acid	C₁₃H₂₃NO₄	详情	详情
(XIII)	27234	(2R)-N-[(1R)-1-benzyl-2-(methylamino)-2-oxoethyl]-N-methyl-2-(methylamino)-3-(2-naphthyl)propanamide	C₂₅H₂₉N₃O₂	详情	详情
(XIV)	27821	(E)-3-(4-hydroxyphenyl)-2-propenamide	C₉H₉NO₂	详情	详情

Extended Information