(R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate

Base Information

• Chemical Name: (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate
• CAS No.: 1350922-83-6
• Molecular Formula: C₂₂H₂₂N₂O₅
• Molecular Weight: 394.427
• Mol file: 1350922-83-6.mol

Synonyms:(R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate

Chemical Property of (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate

There total 4 articles about (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate 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: 70.0%

phthalimide (136918-14-4,85-41-6) + (R)-benzyl [4-oxo-hex-5-en-2-yl]carbamate (1350922-82-5) → (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate (1350922-83-6)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide;

DOI:10.1016/j.tetlet.2011.09.148

Reference yield:

methyl (R)-3-(benzyloxycarbonylamino)-butanoate (142035-70-9) → (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate (1350922-83-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / methanol; water / 3 h / 20 °C

2.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 20 °C

2.2: 17 h / 20 °C

3.1: tetrahydrofuran / 1 h / 0 °C

4.1: N-benzyl-trimethylammonium hydroxide / ethyl acetate / 3 h / Reflux

With N-benzyl-trimethylammonium hydroxide; 1,1'-carbonyldiimidazole; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1002/ejoc.201200919

Reference yield:

(R)-3-(((benzyloxy)carbonyl)amino)butanoic acid (67843-72-5) → (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate (1350922-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 20 °C

1.2: 17 h / 20 °C

2.1: tetrahydrofuran / 1 h / 0 °C

3.1: N-benzyl-trimethylammonium hydroxide / ethyl acetate / 3 h / Reflux

With N-benzyl-trimethylammonium hydroxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1002/ejoc.201200919

upstream raw materials:

phthalimide

(R)-benzyl [4-oxo-hex-5-en-2-yl]carbamate

methyl (R)-3-(benzyloxycarbonylamino)-butanoate

(R)-3-(((benzyloxy)carbonyl)amino)butanoic acid

Downstream raw materials:

benzyl (7S,8S,10R)-10-methyl-8-propyl-7-[(2,2,2-trifluoroacetamido)methyl]-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

benzyl (7S,8S,10R)-7-(aminomethyl)-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

benzyl (7S,8S,10R)-7-[(2,6-dioxopiperidin-1-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

C₂₆H₃₈N₂O₆