Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate

Base Information

• Chemical Name: Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate
• CAS No.: 124842-29-1
• Molecular Formula: C9H14N2O4
• Molecular Weight: 214.221
• DSSTox Substance ID: DTXSID401186192
• Mol file: 124842-29-1.mol

Synonyms:124842-29-1;Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate;Carbamic acid, N-[(3S)-2,5-dioxo-3-pyrrolidinyl]-, 1,1-dimethylethyl ester;(S)-3-(Boc-amino)pyrrolidine-2,5-dione;SCHEMBL4760856;AMY6752;DTXSID401186192;AC9030;(S)-tert-Butyl(2,5-dioxopyrrolidin-3-yl)carbamate;(S)-tert-Butyl (2,5-dioxopyrrolidin-3-yl)carbamate;1,1-Dimethylethyl N-[(3S)-2,5-dioxo-3-pyrrolidinyl]carbamate

Chemical Property of Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 214.09535693
• Heavy Atom Count: 15
• Complexity: 306

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CC(=O)NC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1CC(=O)NC1=O

Technology Process of Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-yl]carbamate

There total 5 articles about Tert-butyl N-[(3S)-2,5-dioxopyrrolidin-3-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: 85.0%

N-tert-butyloxycarbonylasparagine (7536-55-2) → (S)-2-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione (124842-29-1,163929-77-9)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; Reflux;

DOI:10.1016/j.bmcl.2011.12.048

Reference yield: 45.0%

N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7) → (S)-2-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione (124842-29-1,163929-77-9)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 80 ℃; for 6h;

Reference yield: 45.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7) → (S)-2-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione (124842-29-1,163929-77-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 80 ℃; for 6h;

upstream raw materials:

N-t-butyloxycarbonyl-D-asparagine

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butyloxycarbonylasparagine

Downstream raw materials:

N-benzyl-3-Boc-aminopyrrolidin-2,5-dione

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