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

Base Information

Chemical Name:(3S,6R)-N-1-(tert-butoxycarbonyl)-3-(ethoxycarbonyl)methyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone
CAS No.:213619-66-0
Molecular Formula:C₂₃H₃₂N₂O₅
Molecular Weight:416.517
Hs Code.:

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

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

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

There total 11 articles about (3S,6R)-N-1-(tert-butoxycarbonyl)-3-(ethoxycarbonyl)methyl-6-isopropyl-3-methyl-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: 81.0%

: 623-48-3
ethyl iodoacetae

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

: 213619-66-0
(3S,6R)-N-1-(tert-butoxycarbonyl)-3-(ethoxycarbonyl)methyl-6-isopropyl-3-methyl-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 acetonitrile; at 20 ℃; for 5h;
DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

Reference yield: 68.0%

: 105-36-2
ethyl bromoacetate

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

: 213619-66-0
(3S,6R)-N-1-(tert-butoxycarbonyl)-3-(ethoxycarbonyl)methyl-6-isopropyl-3-methyl-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 acetonitrile; at 20 ℃; for 12h;
DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

Reference yield:

: 22838-58-0
Boc-D-Val-OH

: 213619-66-0
(3S,6R)-N-1-(tert-butoxycarbonyl)-3-(ethoxycarbonyl)methyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

Guidance literature:: Multi-step reaction with 7 steps

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

2.1: tetrahydrofuran / 24 h / 20 °C

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

4.1: 95 percent / Et₃N / 3 h / 20 °C

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

6.1: K₂CO₃ / H₂O

6.2: 4-(dimethylamino)pyridine / tetrahydrofuran / 1.5 h / 0 °C

7.1: 68 percent / n-Bu₄NCl; K₂CO₃ / acetonitrile / 12 h / 20 °C

With hydrogenchloride; tetrabutyl-ammonium chloride; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; water; ethyl acetate; acetonitrile; 1.1: Acylation / 2.1: Grignard reaction / 3.1: Hydrolysis / 4.1: Acylation / 5.1: deprotection / 6.1: Cyclization / 6.2: Acylation / 7.1: Alkylation;
DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X