N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide

Base Information

• Chemical Name: N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide
• CAS No.: 142582-32-9
• Molecular Formula: C₂₂H₃₆N₆O₇
• Molecular Weight: 496.564

Synonyms:N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide

Chemical Property of N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide

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Technology Process of N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide

There total 2 articles about N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide 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:

triethyl 1,3,5-triazine-2,4,6-tricarboxylate (898-22-6) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide (142582-32-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / dioxane / 21 h / 101 °C

2: 75 percent / CF₃SO₃H / CH₂Cl₂ / 13 h / 40 °C

3: NaBH₄ / ethanol / 15 h / 25 °C

4: 99 percent / K₂CO₃ / CH₂Cl₂ / 20 h / 25 °C

5: NaHCO₃ / acetonitrile / 10 h / 25 °C

6: aq. NaHCO₃ / tetrahydrofuran / 8 h / 25 °C

With sodium tetrahydroborate; trifluorormethanesulfonic acid; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja00092a012

Reference yield:

triethyl 1,3,5-triazine-2,4,6-tricarboxylate (898-22-6) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide (142582-32-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / dioxane / 21 h / 101 °C

2: 75 percent / CF₃SO₃H / CH₂Cl₂ / 12 h / 40 °C

3: 70 percent / NaBH₄ / ethanol / 150 h / 5 °C

4: 95 percent / K₂CO₃ / CH₂Cl₂ / 17 h / 25 °C

5: NaHCO₃ / acetonitrile / 26 h / 25 °C

6: aq. NaHCO₃ / tetrahydrofuran / 15 h / 25 °C

With sodium tetrahydroborate; trifluorormethanesulfonic acid; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00042a004

Reference yield:

Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanine amide (142582-32-9) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-35-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / LiOH, H₂O / tetrahydrofuran; methanol / 4 h / 25 °C

2: 89 percent / EDCl, HOBt / tetrahydrofuran; dimethylformamide / 72 h / 25 °C

3: 92 percent / LiOH, H₂O / tetrahydrofuran; methanol / 3 h / 25 °C

With lithium hydroxide; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a004

upstream raw materials:

triethyl 1,3,5-triazine-2,4,6-tricarboxylate

Downstream raw materials:

N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

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