2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester

Base Information

• Chemical Name: 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester
• CAS No.: 18668-13-8
• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.426
• Mol file: 18668-13-8.mol

Synonyms:

Chemical Property of 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester

There total 14 articles about 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester 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:

(S)-2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-benzhydryloxycarbonyl-2-methylpropyl ester → 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester (18668-12-7,18668-13-8,18668-14-9,18671-18-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1021/ol048437p

Reference yield:

Z-MeVal-OH (42417-65-2) → 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester (18668-12-7,18668-13-8,18668-14-9,18671-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DCC; DMAP; (1R)-(-)-10-camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

2: TFA / CH₂Cl₂ / 10 h / 0 °C

With dmap; (R)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ol048437p

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 1-carboxy-2-methylpropyl ester (18668-12-7,18668-13-8,18668-14-9,18671-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄; NaNO₂ / H₂O / 0 - 20 °C

2: 60 percent / I₂; iodobenzene diacetate / CH₂Cl₂ / 4 h / -10 - 20 °C

3: 93 percent / DCC; DMAP; (1R)-(-)-10-camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

4: TFA / CH₂Cl₂ / 10 h / 0 °C

With dmap; [bis(acetoxy)iodo]benzene; sulfuric acid; (R)-10-camphorsulfonic acid; iodine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium nitrite; In dichloromethane; water;

DOI:10.1021/ol048437p

upstream raw materials:

N-Benzyloxycarbonyl-N-methyl-D-Val-L-α-hydroxy-isovaleriansaeure-tert.-butylester

Z-D-MeVal

L-α-hydroxyisovaleric acid t-butyl ester

N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester

Downstream raw materials:

(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-methyl-butyric acid (S)-2-methyl-1-[(S)-2-methyl-1-(2,2,2-trichloro-ethoxycarbonyl)-propoxycarbonyl]-propyl ester

N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleryl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester

N-Benzyloxycarbonyl-N-methyl-L-Val-L-α-hydroxy-isovaleryl-N-methyl-L-Val-L-α-hydroxy-isovaleriansaeure-tert.-butylester

Refernces