(R)-2-amino-3-cyclopropylpropanoic acid

Base Information

• Chemical Name: (R)-2-amino-3-cyclopropylpropanoic acid
• CAS No.: 121786-39-8
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2922498590
• DSSTox Substance ID: DTXSID10429389
• Mol file: 121786-39-8.mol

Synonyms:121786-39-8;D-Cyclopropylalanine;(R)-2-amino-3-cyclopropylpropanoic acid;(2R)-2-amino-3-cyclopropylpropanoic acid;D-3-CYCLOPROPYLALANINE;3-Cyclopropyl-D-alanine;D-Cyclopropylalinine;2-Cyclopropyl-D-alanine;MFCD02259520;(R)-2-Amino-3-cyclopropylpropionic acid;H-D-Ala(cPropyl)-OH;H-D-Ala(cyclopropyl)-OH;SCHEMBL2380451;DTXSID10429389;XGUXJMWPVJQIHI-RXMQYKEDSA-N;2-Amino-3-cyclopropyl-propionic acid;AKOS016842388;CS-W013449;AC-24166;AS-15808;EN300-199885;Cyclopropanepropanoic acid, alpha-amino-, (alphaR)-;Q-101763

Chemical Property of (R)-2-amino-3-cyclopropylpropanoic acid

Chemical Property:

• Vapor Pressure: 0.00994mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 258.041 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 109.86 °C
• PSA: 63.32000
• Density: 1.218 g/cm³
• LogP: 0.89870
• Storage Temp.: -15°C
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

≥98%, ^*data from raw suppliers

D-Cyclopropylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CC(C(=O)O)N
• Isomeric SMILES: C1CC1C[C@H](C(=O)O)N
• Uses: D-Cyclopropylalanine is used in the synthesis of heterocyclo-fused [1,3]oxazepines and -thiazepines and analogs as inhibitors of neutral endopeptidase and angiotensin converting enzyme.

Technology Process of (R)-2-amino-3-cyclopropylpropanoic acid

There total 5 articles about (R)-2-amino-3-cyclopropylpropanoic 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: 79.0%

(R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide (170642-22-5) → L(D)-2-amino-4-hexenoic acid (17298-83-8) + (R)-2-amino-3-cyclopropylpropanoic acid (121786-39-8,15785-52-1)

Guidance literature:

In water; for 12h; Yields of byproduct given; Heating;

DOI:10.1021/ja9624073

Reference yield: 50.0%

N-acetyl-3-cyclopropylalanine (133992-69-5,1374669-61-0) → (R)-2-amino-3-cyclopropylpropanoic acid (121786-39-8,15785-52-1) + (2S)-2-amino-3-cyclopropylpropanoic acid (102735-53-5,15785-52-1) + (R)-2-Acetylamino-3-cyclopropyl-propionic acid (121786-36-5,1374669-61-0) + (S)-2-Acetylamino-3-cyclopropyl-propionic acid (121703-93-3,121786-36-5,133992-69-5,1374669-61-0)

Guidance literature:

With potassium hydroxide; Aspergillus acylase I; Yields of byproduct given; pH 7.5-8.0;

DOI:10.1021/ja00198a055

Reference yield:

cyclopropylmethyl iodide (33574-02-6) + 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide (170115-96-5) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + (R)-2-amino-3-cyclopropylpropanoic acid (121786-39-8,15785-52-1) + (2R)-2-amino-5-hexenoic acid (103067-78-3)

Guidance literature:

With water; lithium chloride; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/ja00137a034

upstream raw materials:

N-acetyl-3-cyclopropylalanine

cyclopropylmethyl iodide

2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide

(R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide

Downstream raw materials:

(R)-2-((tert-butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

Refernces

• 1、 Myers, Andrew G.,Gleason, James L.,Yoon, Taeyoung,Kung, Daniel W.. "Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids". . p. 656 - 673. Retrieved 2007/10/03.
• 2、 Chenault, H. Keith,Dahmer, Juergen,Whitesides, George M.. "Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I". . p. 6354 - 6364. Retrieved 2007/10/02.