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

Base Information

• Chemical Name: (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone
• CAS No.: 298704-91-3
• Molecular Formula: C₂₀H₂₈N₂O₄
• Molecular Weight: 360.453

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-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: 71.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (3S,6R)-N-1-Boc-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone (213619-60-4) → (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone (298704-91-3) + (3R,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone

Guidance literature:

With tetrabutyl-ammonium chloride; potassium carbonate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

Reference yield:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) → (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone (298704-91-3)

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: 71 percent / n-Bu₄NCl; K₂CO₃ / acetonitrile / 16 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; 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: hydroxymethylation;

DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

Reference yield:

Boc-D-Val-OH (22838-58-0) → (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone (298704-91-3)

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: 71 percent / n-Bu₄NCl; K₂CO₃ / acetonitrile / 16 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: hydroxymethylation;

DOI:10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X

upstream raw materials:

formaldehyd

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

D-Val-OH

Boc-D-Val-OH

Downstream raw materials:

(S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid

(R)-(-)-2-methylserine

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