(s)-2-Amino-3-cyclopropylpropanoic acid

Base Information

• Chemical Name: (s)-2-Amino-3-cyclopropylpropanoic acid
• CAS No.: 102735-53-5
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2922499990
• European Community (EC) Number: 676-188-9
• DSSTox Substance ID: DTXSID00426241
• Nikkaji Number: J1.787.824G
• Wikidata: Q72460639
• Metabolomics Workbench ID: 117675
• ChEMBL ID: CHEMBL4063034
• Mol file: 102735-53-5.mol

Synonyms:102735-53-5;L-Cyclopropylalanine;(s)-2-amino-3-cyclopropylpropanoic acid;(2S)-2-amino-3-cyclopropylpropanoic acid;L-3-cyclopropylalanine;h-beta-cyclopropyl-l-ala-oh;3-cyclopropyl-L-alanine;(s)-2-amino-3-cyclopropylpropionic acid;3-cyclopropylalanine;CYCLOPROPYLALANINE;l-cyclopropyl alanine;(S)-3-Cyclopropylalanine;(S)-2-Amino-3-cyclopropyl-propionic acid;l-beta-cyclopropylalanine;MFCD00798687;H-Ala(cPropyl)-OH;h-ala(cyclopropyl)-oh;l-ala(3-cyclopropyl);(2s)-2-amino-3-cyclopropyl-propionic acid;D-3-(Cyclopropyl)alanine;(l)-beta-cyclopropylalanine;(s)-beta-cyclopropylalanine;SCHEMBL75669;H-|?-cyclopropyl-L-Ala-OH;CHEMBL4063034;l-cyclopropylalanine, AldrichCPR;DTXSID00426241;XGUXJMWPVJQIHI-YFKPBYRVSA-N;BCP07233;AKOS012011074;AC-6724;AM83659;CS-W008028;GS-6354;HY-W008028;(s)-2-amino-3-cyclopropylpropanoicacid;2-(s)-amino-3-cyclopropyl propanoic acid;2-(s)amino-3-(cyclopropyl)propanoic acid;Cyclopropanepropanoic acid, ?-amino-, (?S)-;EN300-206597;Cyclopropanepropanoic acid, alpha-amino-, (alphaS)-;Q-101766

Chemical Property of (s)-2-Amino-3-cyclopropylpropanoic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00994mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 258 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 109.9 °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%,99%, ^*data from raw suppliers

3-Cyclopropyl-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CC(C(=O)O)N
• Isomeric SMILES: C1CC1C[C@@H](C(=O)O)N
• Uses: 3-Cyclopropyl-L-alanine is used to prepare optically active pyrrolidineacetic acids as CCR5 receptor antagonists with antiviral activity against HIV.

Technology Process of (s)-2-Amino-3-cyclopropylpropanoic acid

There total 14 articles about (s)-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: 92.0%

N-acetyl-3-cyclopropylalanine (133992-69-5,1374669-61-0) → (2S)-2-amino-3-cyclopropylpropanoic acid (102735-53-5,15785-52-1)

Guidance literature:

With sodium hydroxide; porcine pancreatic acylase I; In water; at 37 ℃; for 4h;

DOI:10.1080/00397919608003718

Reference yield: 83.0%

(S)-2-amino-3-cyclopropylpropionic acid benzyl ester (113741-17-6) → (2S)-2-amino-3-cyclopropylpropanoic acid (102735-53-5,15785-52-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 50 ℃; for 3h; under 2068.59 Torr;

DOI:10.1016/j.tetasy.2003.07.007

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

upstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester

N-acetyl-3-cyclopropylalanine

(S)-2-amino-3-cyclopropylpropionic acid benzyl ester

2-tert-butoxycarbonylamino-3-cyclopropylacrylic acid benzyl ester

Downstream raw materials:

L-leucine

L-Norleucine

(S)-3-Cyclopropyl-2-[((2S,6R)-2,6-dimethyl-piperidine-1-carbonyl)-amino]-propionic acid benzyl ester

2-(S)-hydroxy-3-(cyclopropyl)propanoic acid

Refernces

• 1、 Boaz, Neil W.,Debenham, Sheryl D.,Mackenzie, Elaine B.,Large, Shannon E.. "Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis". . p. 2421 - 2424. Retrieved 2002.
• 2、 Boaz, Neil W.,Debenham, Sheryl D.,Large, Shannon E.,Moore, Mary K.. "The preparation of enantiomerically pure cyclopropylalanine". . p. 3575 - 3580. Retrieved 2007/10/03.