(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

Base Information

Chemical Name:(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide
CAS No.:611210-37-8
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

Synonyms:(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

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Chemical Property of (2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

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Technology Process of (2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

There total 6 articles about (2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

: 13748-90-8,498-36-2
(S)-2-hydroxyl-3,3-dimethylbutyric acid

: 611210-21-0
(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethanamine

: 611210-37-8
(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/j.bmc.2003.09.031

Reference yield:

: 13512-31-7
N-(benzyloxycarbonyl)-L-tyrosine methyl ester

: 611210-37-8
(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

2: 84 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

3: 66 percent / pyridinium tosylate / toluene / 18 h / 80 °C

4: 52 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

5: 50 percent / benzotriazol-1-ol; Et₃N; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2003.09.031

Reference yield:

: 3417-91-2
L-tyrosine methyl ester HCl

: 611210-37-8
(2S)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / Et₃N / tetrahydrofuran / 18 h / 20 °C

2: 91 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

3: 84 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

4: 66 percent / pyridinium tosylate / toluene / 18 h / 80 °C

5: 52 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

6: 50 percent / benzotriazol-1-ol; Et₃N; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2003.09.031