(S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid

Base Information

• Chemical Name: (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid
• CAS No.: 765299-32-9
• Molecular Formula: C₁₇H₂₄N₂O₆
• Molecular Weight: 352.387
• Mol file: 765299-32-9.mol

Synonyms:(S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid

Chemical Property of (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid

There total 7 articles about (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-N2-carbobenzoxy-N2-methyl-2,3-diaminopropionic acid (147634-99-9) → (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid (765299-32-9)

Guidance literature:

With sodium hydroxide; sodium carbonate; In tert-butyl alcohol; at 0 - 20 ℃; for 3.5h; pH=9;

DOI:10.1016/j.tet.2004.06.034

Reference yield:

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate (60079-12-1) → (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid (765299-32-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Ag₂O / dimethylformamide / 7 h / 20 °C

2.1: LiOH*H₂O / aq. methanol / 5 - 20 °C

3.1: 97 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 5 °C

4.1: 84 percent / aq. NH₃ / tetrahydrofuran / 0 - 20 °C

5.1: 58 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

6.1: TFA / CH₂Cl₂ / 4 h / 20 °C

6.2: 75 percent / PhI(OCOCF₃)2; pyridine / dimethylformamide; H₂O / 16 h / 20 °C

7.1: 97 percent / aq. NaOH; Na₂CO₃ / 2-methyl-propan-2-ol / 3.5 h / 0 - 20 °C / pH 9

With lithium hydroxide; ammonium hydroxide; sodium hydroxide; sodium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2004.06.034

Reference yield:

N2-benzyloxycarbonyl-N2-methyl-L-asparagine (475296-58-3) → (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid (765299-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA / CH₂Cl₂ / 4 h / 20 °C

1.2: 75 percent / PhI(OCOCF₃)2; pyridine / dimethylformamide; H₂O / 16 h / 20 °C

2.1: 97 percent / aq. NaOH; Na₂CO₃ / 2-methyl-propan-2-ol / 3.5 h / 0 - 20 °C / pH 9

With sodium hydroxide; sodium carbonate; trifluoroacetic acid; In dichloromethane; tert-butyl alcohol;

DOI:10.1016/j.tet.2004.06.034

upstream raw materials:

di-tert-butyl dicarbonate

(2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

N²-benzyloxycarbonyl-N²-methyl-L-asparagine

Downstream raw materials:

C₂₀H₂₉N₅O₆S