3-Boc-amino-2,6-dioxopiperidine

Base Information

• Chemical Name: 3-Boc-amino-2,6-dioxopiperidine
• CAS No.: 31140-42-8
• Molecular Formula: C10H16N2O4
• Molecular Weight: 228.248
• Hs Code.: 2925190090
• European Community (EC) Number: 808-650-4
• DSSTox Substance ID: DTXSID10953235
• Mol file: 31140-42-8.mol

Synonyms:3-Boc-amino-2,6-dioxopiperidine;31140-42-8;tert-butyl (2,6-dioxopiperidin-3-yl)carbamate;MFCD08275101;TERT-BUTYL N-(2,6-DIOXOPIPERIDIN-3-YL)CARBAMATE;TERT-BUTYL 2,6-DIOXOPIPERIDIN-3-YLCARBAMATE;(S)-3-(Boc-amino)piperidine-2,6-dione;Tert-butyl N-(2,6-dioxo-3-piperidyl)carbamate;SCHEMBL2176628;DTXSID10953235;TUGRLMXVKASPTN-UHFFFAOYSA-N;BCP17754;BGA36792;3-(Boc-amino)piperidine-2,6-dione;Carbamic acid, (2,6-dioxo-3-piperidinyl)-, 1,1-dimethylethyl ester;MFCD24465586;AKOS015152167;AB44751;AB88561;AB89218;AC-29735;DS-11389;SY108823;SY292543;3-Boc-Amino-2 pound not6-dioxopiperidine;CS-0036724;FT-0659617;2,6-Dioxo-3-(t-butoxycarbonylamino)piperidine;W12030;2,6-dioxo-3-(t-butoxycarbonylamino)-piperidine;3-(tert-Butoxycarbonylamino)-2,6-piperidinedione;tert-Butyl hydrogen (6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)carbonimidate

Chemical Property of 3-Boc-amino-2,6-dioxopiperidine

Chemical Property:

• Vapor Pressure: 2.32E-07mmHg at 25°C
• Melting Point: 193.7-194.4 °C
• Boiling Point: 423 °C at 760 mmHg
• PKA: 10.78±0.20(Predicted)
• Flash Point: 209.6 °C
• PSA: 84.50000
• Density: 1.2 g/cm³
• LogP: 1.03600
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly, Heated), DMF (Slightly), DMSO (Slightly), Methanol (Slight
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 228.11100700
• Heavy Atom Count: 16
• Complexity: 319

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl 2,6-dioxopiperidin-3-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCC(=O)NC1=O
• Uses: tert-Butyl (2,6-Dioxopiperidin-3-yl)carbamate is an intermediate in the synthesis of Thalidomide-d4 (T338852), a labelled Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.

Technology Process of 3-Boc-amino-2,6-dioxopiperidine

There total 10 articles about 3-Boc-amino-2,6-dioxopiperidine 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: 99.0%

5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid (85535-45-1) → (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8)

Guidance literature:

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

DOI:10.3390/molecules26092525

Reference yield: 95.0%

1-[(tert-butoxy)-carbonyl-amino]propane-1,3-dicarboxylic acid (120341-33-5) → (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8)

Guidance literature:

With 2,2,2-trifluoroacetamide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; at 20 ℃;

DOI:10.1016/j.bmcl.2008.11.118

Reference yield: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + rac-α-aminoglutarimide hydrochloride (24666-56-6,2686-86-4) → (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8)

Guidance literature:

rac-α-aminoglutarimide hydrochloride; With triethylamine; In dichloromethane; at 50 ℃; for 0.5h; Sealed tube; Microwave irradiation;

di-tert-butyl dicarbonate; In dichloromethane; at 0 ℃; for 0.5h;

upstream raw materials:

Boc-Gln-OH

1-[(tert-butoxy)-carbonyl-amino]propane-1,3-dicarboxylic acid

5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid

(S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate

Downstream raw materials:

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Lenalidomide

2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

rac-α-aminoglutarimide hydrochloride

Refernces

• 1、 -. "GPX4 protein degradation agent, preparation method and application thereof, and antitumor cell drug". Paragraph 0296-0297; 0304-0305. . Retrieved 2021/09/04.
• 2、 Bemis, Troy A.,La Clair, James J.,Burkart, Michael D.. "Traceless Staudinger ligation enabled parallel synthesis of proteolysis targeting chimera linker variants". supporting information. p. 1026 - 1029. Retrieved 2021/02/06.