diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate

Base Information

• Chemical Name: diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate
• CAS No.: 173037-34-8
• Molecular Formula: C₂₅H₃₃N₅O₆S
• Molecular Weight: 531.633

Synonyms:diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate

Chemical Property of diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate

Chemical Property:

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Technology Process of diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate

There total 10 articles about diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate 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: 27.0%

5-bromo-2,6-diamino-4(3H)-pyrimidinone (6312-72-7) + diethyl N-<4-(trans-2-(mercaptomethyl)cyclobutyl)benzoyl>-L-glutamate (173037-33-7) → diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate (173037-34-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 85 ℃; for 0.833333h;

DOI:10.1002/jhet.5570320514

Reference yield:

4-bromophenyl 2-chloroethyl ketone (31736-73-9) → diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate (173037-34-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 94 percent / NaBH₄ / tetrahydrofuran; ethanol / 0.17 h / -5 °C

2: 94 percent / 48percent aq. HBr / 3 h / Ambient temperature

3: 50 percent / NaH / dioxane / 6 h / Heating

4: aq.LiCl / dimethylsulfoxide / 4 h / Heating

5: 2M NaOEt / 24 h / Ambient temperature

6: BH₃ / tetrahydrofuran / 16 h / 0 - 20 °C

7: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

8: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to -10 deg C, 2.) THF, hexane, 45 min

9: 1-hydroxybenzotriazole, diisopropylethylamine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 18 h / Ambient temperature

10: 65 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

11: 89 percent / CBr₄, Ph₃P / CH₂Cl₂ / 16 h / 6 - 20 °C

12: 92 percent / acetone / 0.42 h / Heating

13: 97 percent / HCl / ethanol / 2 h / Heating

14: 27 percent / diisopropylethylamine / dimethylformamide / 0.83 h / 85 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; borane; tetrabutyl ammonium fluoride; hydrogen bromide; sodium ethanolate; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1002/jhet.5570320514

Reference yield:

1-bromo-4-(1-bromo-3-chloropropyl)benzene (173037-26-8) → diethyl N-<4-(trans-2-<(<2,6-diamino-4-(3H)-oxopyrimidin-5-yl>thio)methyl>cyclobutyl)benzoyl>L-glutamate (173037-34-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 50 percent / NaH / dioxane / 6 h / Heating

2: aq.LiCl / dimethylsulfoxide / 4 h / Heating

3: 2M NaOEt / 24 h / Ambient temperature

4: BH₃ / tetrahydrofuran / 16 h / 0 - 20 °C

5: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

6: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to -10 deg C, 2.) THF, hexane, 45 min

7: 1-hydroxybenzotriazole, diisopropylethylamine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 18 h / Ambient temperature

8: 65 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 89 percent / CBr₄, Ph₃P / CH₂Cl₂ / 16 h / 6 - 20 °C

10: 92 percent / acetone / 0.42 h / Heating

11: 97 percent / HCl / ethanol / 2 h / Heating

12: 27 percent / diisopropylethylamine / dimethylformamide / 0.83 h / 85 °C

With hydrogenchloride; dmap; n-butyllithium; carbon tetrabromide; borane; tetrabutyl ammonium fluoride; sodium ethanolate; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1002/jhet.5570320514

upstream raw materials:

5-bromo-2,6-diamino-4(3H)-pyrimidinone

diethyl N-<4-(trans-2-(mercaptomethyl)cyclobutyl)benzoyl>-L-glutamate

4-bromophenyl 2-chloroethyl ketone

1-bromo-4-(1-bromo-3-chloropropyl)benzene

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