N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide

Base Information

• Chemical Name: N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide
• CAS No.: 511544-99-3
• Molecular Formula: C₄₆H₇₂N₁₀O₉
• Molecular Weight: 909.139

Synonyms:N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide

Chemical Property of N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide

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Technology Process of N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide

There total 10 articles about N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide 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: 61.0%

(S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid (79640-70-3) + N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide (167986-15-4) → Nα-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide (511544-99-3)

Guidance literature:

(S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 5h;

DOI:10.1071/CH02125

Reference yield:

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid (2528-30-5) → Nα-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide (511544-99-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: SOCl₂ / toluene / 4 h / Heating

2.1: 99 percent / (i-Pr)2NEt / dioxane; H₂O / 0 - 20 °C

3.1: 90 percent / H₂ / Pd/C / ethanol

4.1: 86 percent / dimethylformamide / 31 h / 20 °C

5.1: DCC; N-hydroxysuccinimide / dimethylformamide / 16 h / 20 °C

5.2: 61 percent / Et₃N / dimethylformamide; CH₂Cl₂ / 5 h

With 1-hydroxy-pyrrolidine-2,5-dione; thionyl chloride; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1071/CH02125

Reference yield:

benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate (66891-86-9) → Nα-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide (511544-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / (i-Pr)2NEt / dioxane; H₂O / 0 - 20 °C

2.1: 90 percent / H₂ / Pd/C / ethanol

3.1: 86 percent / dimethylformamide / 31 h / 20 °C

4.1: DCC; N-hydroxysuccinimide / dimethylformamide / 16 h / 20 °C

4.2: 61 percent / Et₃N / dimethylformamide; CH₂Cl₂ / 5 h

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1071/CH02125

upstream raw materials:

(S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid

N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide

L-glutamic acid 1-tert-butyl ester 5-methyl ester

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

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