4-Carbamoyl-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)butanoic acid

Base Information

• Chemical Name: 4-Carbamoyl-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)butanoic acid
• CAS No.: 2110-19-2
• Deprecated CAS: 2110-19-2
• Molecular Formula: C₁₃H₁₂N₂O₅
• Molecular Weight: 276.249
• Hs Code.: 2925190090
• NSC Number: 527451
• ChEMBL ID: CHEMBL1012
• Mol file: 2110-19-2.mol

Synonyms:7607-72-9;4-CARBAMOYL-2-(1,3-DIOXO-2,3-DIHYDRO-1H-ISOINDOL-2-YL)BUTANOIC ACID;5-Amino-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic Acid;N-Phthalyl-D-glutamine;N-Phthalyl-DL-glutamine;N-Phthaloyl-DL-glutamine;2-Phthalimidoglutaramic acid;MFCD00422111;5-amino-2-(1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid;2H-Isoindole-2-acetic acid, alpha-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-;N-Phthalyl-L-glutamine;174591-46-9;MFCD00190993;N-Phthalylglutamin;Glutaramic acid, DL-;CHEMBL1012;SCHEMBL410627;Glutaramic acid, (.+-.)-;N-alpha-phthaloyl-DL-glutamine;dl-2-Phthalimidoglutaramic acid;2-Phthalimido-DL-glutaramic acid;N-.alpha.-Phthaloyl-DL-glutamine;AC6772;MFCD30729879;NSC527451;WU-309;AKOS000155343;AKOS022507527;BA 2738;Glutaramic acid, 2-phthalimido-, DL-;NSC 527451;NSC-527451;SB64087;2110-19-2;AC-29911;CS-12469;SY059199;SY059781;SY059784;Glutaramic acid, 2-phthalimido-, (+-)-;FT-0634787;EN300-91643;A923187;Z277469450;2H-Isoindole-2-acetic acid,3-dihydro-1,3-dioxo-, (.+-.)-;2H-Isoindole-2-acetic acid, alpha-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-, (+-)-;4-CARBAMOYL-2-(1,3-DIOXO-2,3-DIHYDRO-1H-ISOINDOL-2-YL)BUTANOICACID;alpha-(3-Amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid

Chemical Property of 4-Carbamoyl-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)butanoic acid

Chemical Property:

• Vapor Pressure: 3.27E-15mmHg at 25°C
• Boiling Point: 599.3°Cat760mmHg
• Flash Point: 316.3°C
• PSA: 117.77000
• Density: 1.508g/cm³
• LogP: 0.63950
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 276.07462149
• Heavy Atom Count: 20
• Complexity: 438

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-CARBAMOYL-2-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-BUTYRIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)C(CCC(=O)N)C(=O)O

Technology Process of 4-Carbamoyl-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)butanoic acid

There total 12 articles about 4-Carbamoyl-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)butanoic 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: 76.0%

N-phthaloylglutamic acid anhydride (3343-28-0,3085-92-5) → 2-phthalimidoglutaramic acid (7607-72-9,2110-19-2,174591-46-9)

Guidance literature:

With ammonia; at 20 ℃; for 0.333333h;

DOI:10.1016/j.molstruc.2020.128600

Reference yield: 72.0%

phthalic anhydride (85-44-9) + L-glutamine (56-85-9,26700-71-0) → (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

phthalic anhydride; L-glutamine; In N,N-dimethyl-formamide; at 90 - 95 ℃; for 3h;

With hydrogenchloride; water; at 15 ℃; for 2h; pH=1.2;

Reference yield: 67.0%

L-glutamine (56-85-9,26700-71-0) + N-ethoxycarbonylphthalimide (22509-74-6) → (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

L-glutamine; N-ethoxycarbonylphthalimide; With sodium carbonate; In water; for 1h; Inert atmosphere;

With hydrogenchloride; In water; for 1h;

DOI:10.1021/op980201b

upstream raw materials:

N-phthaloyl-L-glutamic anhydride

(S)-thalidomide

phthalic anhydride

L-glutamine

Downstream raw materials:

N²,N²-phthaloyl-glutamine-methyl ester

thalidomide

Refernces

• 1、 -. "CRYSTALLINE FORMS OF THALIDOMIDE AND PROCESSES FOR THEIR PREPARATION". Page/Page column 24-25. . Retrieved 2012/01/05.
• 2、 -. "PROCESSES FOR THE PREPARATION OF THALIDOMIDE". Page/Page column 12-15. . Retrieved 2009/08/14.