2-(1-Amino-1-carboxyethyl)cyclopropane-1-carboxylic acid

Base Information

• Chemical Name: 2-(1-Amino-1-carboxyethyl)cyclopropane-1-carboxylic acid
• CAS No.: 157141-16-7
• Molecular Formula: C₇H₁₁NO₄
• Molecular Weight: 173.169
• ChEMBL ID: CHEMBL412445
• DSSTox Substance ID: DTXSID20599320
• Nikkaji Number: J829.150K
• Mol file: 157141-16-7.mol

Synonyms:2-(1-AMINO-1-CARBOXYETHYL)CYCLOPROPANE-1-CARBOXYLIC ACID;157141-16-7;(2S,3S,4S)-2-METHYL-2-(CARBOXYCYCLOPROPYL)GLYCINE;CHEMBL412445;SCHEMBL7331950;DTXSID20599320;BDBM50102111;J-009382;2-(1-Amino-1-carboxy-ethyl)-cyclopropanecarboxylic acid

Chemical Property of 2-(1-Amino-1-carboxyethyl)cyclopropane-1-carboxylic acid

Chemical Property:

• PSA: 100.62000
• LogP: 0.20940
• Storage Temp.: −20°C
• Solubility.: H2O: >10 mg/mL
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 240

Purity/Quality:

99.3% ^*data from raw suppliers

(2S,3S,4S)-2-Methyl-2-(carboxycyclopropyl)glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CC1C(=O)O)(C(=O)O)N
• Uses: (2S,3S,4S)-2-Methyl-2-(carboxycyclopropyl)glycine is an antagonist of group II metabotropic glutamate receptors (mGluRs).

Technology Process of 2-(1-Amino-1-carboxyethyl)cyclopropane-1-carboxylic acid

There total 7 articles about 2-(1-Amino-1-carboxyethyl)cyclopropane-1-carboxylic 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: 86.0%

(1S,2S)-2-((S)-1-Benzoylamino-1-carboxy-ethyl)-cyclopropanecarboxylic acid → (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine (157141-16-7)

Guidance literature:

With hydrogenchloride; methyloxirane; at 100 ℃; for 48h;

DOI:10.1016/S0957-4166(97)00031-1

Reference yield: 85.0%

(2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine (537040-14-5) → (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine (157141-16-7)

Guidance literature:

With hydrogen bromide; acetic acid; at 20 ℃; for 1.5h;

DOI:10.1016/S0957-4166(03)00049-1

Reference yield:

(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one (537040-12-3) → (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine (157141-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / Pd(OAc)2 / diethyl ether / 20 °C

2: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

3: 85 percent / 32 percent HBr; AcOH / 1.5 h / 20 °C

With lithium hydroxide; hydrogen bromide; acetic acid; palladium diacetate; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0957-4166(03)00049-1

upstream raw materials:

(2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine

(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one

(E)-3-((2R,4S)-3-Benzoyl-4-methyl-5-oxo-2-phenyl-oxazolidin-4-yl)-acrylic acid methyl ester

(1S,2S)-2-((2R,4S)-3-Benzoyl-4-methyl-5-oxo-2-phenyl-oxazolidin-4-yl)-cyclopropanecarboxylic acid methyl ester