methyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethanoate -Drug Synthesis Database

【结构式】

【分子编号】59932

【品名】methyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethanoate

【CA登记号】

【分子式】C₁₅H₂₃ClO₃Si

【分子量】314.88402

【元素组成】C 57.22% H 7.36% Cl 11.26% O 15.24% Si 8.92%

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)

Esterification of (R)-3-chloromandelic acid (I) with MeOH and H2SO4 to yield ether (II), followed by hydroxyl group silylation using t-butyldimethylsilyl chloride and imidazole furnished (III). Reduction of the ester function of (III) by means of DIBAL produced aldehyde (IV), which was subjected to reductive amination with D-alanine methyl ester (V) to produce amino ester (VI). After protection of the amino group of (VI) as the N-Boc derivative (VII), further DIBAL reduction of the ester group afforded aldehyde (VIII).

参考文献中间体

合成目标

【1】 Uehling, D.E.; Donaldson, K.H.; Deaton, D.N.; Hyman, C.E.; Sugg, E.E.; Barret, D.G.; Hughes, R.G.; Reitter, B.; Adkison, K.K.; Lancaster, M.E.; Lee, F.; Hart, R.; Paulik, M.A.; Sherman, B.W.; True, T.; Cowan, C.; Synthesis and evaluation of potent and selective beta3 adrenergic receptor agonists containing acylsulfonamide, sulfonylsulfonamide, and sulfonylurea carboxylic acid isosteres. J Med Chem 2002, 45, 3, 567.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	59930	(2R)-2-(3-chlorophenyl)-2-hydroxyethanoic acid	C₈H₇ClO₃	详情	详情
(II)	59931	methyl (2R)-2-(3-chlorophenyl)-2-hydroxyethanoate	C₉H₉ClO₃	详情	详情
(III)	59932	methyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethanoate	C₁₅H₂₃ClO₃Si	详情	详情
(IV)	59933	(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethanal	C₁₄H₂₁ClO₂Si	详情	详情
(V)	20694	methyl (2S)-2-aminopropanoate	C₄H₉NO₂	详情	详情
(VI)	59934	methyl (2R)-2-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl]amino}propanoate	C₁₈H₃₀ClNO₃Si	详情	详情
(VII)	59935	methyl (2R)-2-{(tert-butoxycarbonyl)[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl]amino}propanoate	C₂₃H₃₈ClNO₅Si	详情	详情
(VIII)	59936	tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-oxoethyl]carbamate	C₂₂H₃₆ClNO₄Si	详情	详情

Extended Information