N-carbamoylmethionine

Base Information

• Chemical Name: N-carbamoylmethionine
• CAS No.: 54896-74-1
• Molecular Formula: C6H12N2O3S
• Molecular Weight: 192.239
• European Community (EC) Number: 841-082-5
• DSSTox Substance ID: DTXSID50365095
• Nikkaji Number: J365.275K
• Wikidata: Q82149492
• Mol file: 54896-74-1.mol

Synonyms:N-carbamoyl-methionine;N-carbamoylmethionine;N-carbamylmethionine

Chemical Property of N-carbamoylmethionine

Chemical Property:

• Melting Point: 171-172 °C
• Boiling Point: 401.5±45.0 °C(Predicted)
• PSA: 117.72000
• Density: 1.315±0.06 g/cm3(Predicted)
• LogP: 0.95220
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 192.05686342
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

N-Carbamoylmethionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)O)NC(=O)N
• Isomeric SMILES: CSCC[C@@H](C(=O)O)NC(=O)N

Technology Process of N-carbamoylmethionine

There total 9 articles about N-carbamoylmethionine 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: 98.0%

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione (13253-44-6) → L-methionine (63-68-3,26062-47-5,58576-49-1) + (S)-N-carbamoylmethionine (54896-74-1)

Guidance literature:

In water; at 30 ℃; for 72h; Mechanism; Pseudomonas sp. strain NS₆₇₁, air. pH 7.0 - 7.2; different cultivation times, other 5-substituted hydantoins;

Reference yield: 85.0%

potassium cyanate (590-28-3) + L-methionine (63-68-3,26062-47-5,58576-49-1) → (S)-N-carbamoylmethionine (54896-74-1)

Guidance literature:

In water; at 80 ℃; for 1h; Microwave irradiation;

DOI:10.1055/s-0030-1258553

Reference yield: 80.0%

L-methionine (63-68-3,26062-47-5,58576-49-1) + urea (57-13-6) → (S)-N-carbamoylmethionine (54896-74-1)

Guidance literature:

With sodium hydroxide; for 0.0666667h; microwave irradiation;

DOI:10.1080/00397910701317068

upstream raw materials:

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

5-[2-(methylthio)ethyl]-2,4-imidazolidinedione

(R)-5-(2-Methylsulfanyl-ethyl)-imidazolidine-2,4-dione

2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide

Downstream raw materials:

(-)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-(methylthio)butanoic acid

(+)-(S)-2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-(methylthio)butanoic acid

2,4-imidazolidinedione

5-[2-(methylthio)ethyl]-2,4-imidazolidinedione

Refernces

• 1、 De Luca, Lidia,Porcheddu, Andrea,Giacomelli, Giampaolo,Murgia, Irene. "Microwave-assisted synthesis of N-monosubstituted urea derivatives". scheme or table. p. 2439 - 2442. Retrieved 2010/11/18.
• 2、 Ishikawa, Takahiro,Watabe, Ken,Mukohara, Yukuo,Nakamura, Hiroaki. "Mechanism of stereospecific conversion of DL-5-substituted hydantoins to the corresponding L-amino acids by Pseudomonas sp. strain NS671". . p. 185 - 187. Retrieved 2007/10/03.