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

Base Information

• Chemical Name: 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
• CAS No.: 142582-34-1
• Molecular Formula: C₄₆H₅₅N₉O₉
• Molecular Weight: 877.998

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 8 articles about 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 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: 89.0%

Nα,Nβ-bis(tert-butoxycarbonyl)-Nβ-<(4-amino-6-carboxy-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanineamide (129812-61-9) + erythro-N?-Triphenylmethyl-β-hydroxy-L-histidinmethylester (142582-33-0) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-34-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 72h;

DOI:10.1021/jo00042a004

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-34-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 96 percent / LiOH, H₂O / tetrahydrofuran; methanol / 4 h / 25 °C

3: 89 percent / EDCl, HOBt / tetrahydrofuran; dimethylformamide / 72 h / 25 °C

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

DOI:10.1021/jo00042a004

Reference yield:

2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine (117663-59-9) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-34-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / CF₃SO₃H / CH₂Cl₂ / 12 h / 40 °C

2: 70 percent / NaBH₄ / ethanol / 150 h / 5 °C

3: 95 percent / K₂CO₃ / CH₂Cl₂ / 17 h / 25 °C

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

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

6: 96 percent / LiOH, H₂O / tetrahydrofuran; methanol / 4 h / 25 °C

7: 89 percent / EDCl, HOBt / tetrahydrofuran; dimethylformamide / 72 h / 25 °C

With lithium hydroxide; sodium tetrahydroborate; trifluorormethanesulfonic acid; water; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00042a004

upstream raw materials:

N^α,N^β-bis(tert-butoxycarbonyl)-N^β-<(4-amino-6-carboxy-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanineamide

erythro-N^?-Triphenylmethyl-β-hydroxy-L-histidinmethylester

di-tert-butyl dicarbonate

2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine

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

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