(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

Base Information

Chemical Name:(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone
CAS No.:213619-68-2
Molecular Formula:C₂₃H₃₂N₂O₅
Molecular Weight:416.517
Hs Code.:

Synonyms:(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

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Chemical Property of (3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

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Technology Process of (3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

There total 11 articles about (3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone 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: 62.0%

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 213619-60-4
(3S,6R)-N-1-Boc-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

: 213619-68-2
(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

: (3R,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

: (6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone C-3 dimer

Guidance literature:: With tetrabutyl-ammonium chloride; potassium carbonate; In dichloromethane; at 20 ℃; for 19h;
DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

Reference yield: 62.0%

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: (R)-6-Isopropyl-3-methyl-2-oxo-5-phenyl-3,6-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester

: 213619-68-2
(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

Guidance literature:: With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; for 19h; Ambient temperature;
DOI:10.1016/S0957-4166(98)00208-0

Reference yield:

: 640-68-6,25609-85-2,7004-03-7,921-10-8
D-Val-OH

: 213619-68-2
(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-3-(2-methoxycarbonyl)ethyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaHCO₃ / dioxane; H₂O / 12 h / Heating

2.1: Et₃N; N,N,N',N'-tetramethyl-O-(benzotriazol-1-yl)uronium BF₄ / acetonitrile / 20 °C

3.1: tetrahydrofuran / 24 h / 20 °C

4.1: HCl(g) / ethyl acetate / 0.5 h / 20 °C

5.1: 95 percent / Et₃N / 3 h / 20 °C

6.1: HCl(g) / ethyl acetate / 1 h

7.1: K₂CO₃ / H₂O

7.2: 4-(dimethylamino)pyridine / tetrahydrofuran / 1.5 h / 0 °C

8.1: 62 percent / n-Bu₄NCl; K₂CO₃ / CH₂Cl₂ / 19 h / 20 °C

With hydrogenchloride; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; acetonitrile; 1.1: Acylation / 2.1: Acylation / 3.1: Grignard reaction / 4.1: Hydrolysis / 5.1: Acylation / 6.1: deprotection / 7.1: Cyclization / 7.2: Acylation / 8.1: Addition;
DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X