(2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester

Base Information

• Chemical Name: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester
• CAS No.: 108732-31-6
• Molecular Formula: C₁₉H₂₃NO₇
• Molecular Weight: 377.394
• Mol file: 108732-31-6.mol

Synonyms:

Chemical Property of (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester

There total 7 articles about (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl 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)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester (108732-31-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / LiBH₄ / tetrahydrofuran / 15 h / 5 °C

2: 98 percent / TEA, 4-DMAP / dimethylformamide / 3 h / Ambient temperature

3: 90 percent / RuO₂ hydrate, 10percent aqueous NaIO₄ / ethyl acetate / 1 h / Ambient temperature

4: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h

5: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature

6: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH₂Cl₂, 3 h, room temperature

With dmap; ruthenium(IV) oxide; sodium periodate; dipyridinium dichromate; lithium borohydride; n-butyllithium; TEA; toluene-4-sulfonic acid; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester (108732-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / TEA, 4-DMAP / dimethylformamide / 3 h / Ambient temperature

2: 90 percent / RuO₂ hydrate, 10percent aqueous NaIO₄ / ethyl acetate / 1 h / Ambient temperature

3: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h

4: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature

5: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH₂Cl₂, 3 h, room temperature

With dmap; ruthenium(IV) oxide; sodium periodate; dipyridinium dichromate; n-butyllithium; TEA; toluene-4-sulfonic acid; diisopropylamine; dicyclohexyl-carbodiimide; In methanol; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate (81658-26-6) → (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester (108732-31-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1h; 3.) room temperature, 1h

2: 78 percent / p-toluenesulphonic acid / methanol / 2 h / Ambient temperature

3: 1.) pyridinium dichromate; 2.) DCC, 4-DMAP / 1.) DMF, 15 h, 40 deg C; 2.) CH₂Cl₂, 3 h, room temperature

With dmap; dipyridinium dichromate; n-butyllithium; toluene-4-sulfonic acid; diisopropylamine; dicyclohexyl-carbodiimide; In methanol;

upstream raw materials:

methanol

(2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-hydroxymethyl-5-pyrrolidone

N-benzyloxycarbonylimidazole

N-(tert-butoxycarbonyl)-L-prolinol