(S)-2-Amino-2-ethylhexanoic acid ethyl ester

Base Information

• Chemical Name: (S)-2-Amino-2-ethylhexanoic acid ethyl ester
• CAS No.: 164262-42-4
• Molecular Formula: C₁₀H₂₁NO₂
• Molecular Weight: 187.282
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID60433739
• Nikkaji Number: J1.418.903C
• Wikidata: Q82247952
• Mol file: 164262-42-4.mol

Synonyms:164262-42-4;ethyl (2S)-2-amino-2-ethylhexanoate;(S)-2-Amino-2-ethylhexanoic acid ethyl ester;Ethyl 2-ethyl-L-norleucinate;(S)-Ethyl 2-amino-2-ethylhexanoate;ethyl ((s)-2-amino-2-ethyl (hexanoate;ETHYL (S)-2-AMINO-2-ETHYLHEXANOATE;DTXSID60433739;Ethyl(S)-2-amino-2-ethylhexanoate;MFCD05663536;AKOS006294446

Chemical Property of (S)-2-Amino-2-ethylhexanoic acid ethyl ester

Chemical Property:

• PSA: 52.32000
• LogP: 2.54750
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 187.157228913
• Heavy Atom Count: 13
• Complexity: 159

Purity/Quality:

99%min ^*data from raw suppliers

(S)-2-AMINO-2-ETHYLHEXANOIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(CC)(C(=O)OCC)N
• Isomeric SMILES: CCCC[C@@](CC)(C(=O)OCC)N

Technology Process of (S)-2-Amino-2-ethylhexanoic acid ethyl ester

There total 9 articles about (S)-2-Amino-2-ethylhexanoic acid ethyl ester 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: 31.0%

(+/-)-ethyl 2-amino-2-ethylhexanoate (152802-65-8) → (R)-2-amino-2-ethylhexanoic acid (114781-14-5) + ethyl (S)-2-amino-2-ethylhexanoate (164262-42-4)

Guidance literature:

With porcine liver esterase; In phosphate buffer; at 30 ℃; for 7.5h; pH=8.0;

DOI:10.1002/1522-2675(20001004)83:10<2823::AID-HLCA2823>3.0.CO;2-#

Reference yield:

1-iodo-butane (542-69-8) + Ethyl (E)-2-(benzylideneamino) butanoate (78843-65-9) → ethyl (R)-2-amino-2-ethylhexanoate + ethyl (S)-2-amino-2-ethylhexanoate (164262-42-4)

Guidance literature:

1-iodo-butane; ethyl N-benzylidene-2-aminobutanoate; With cesium oxide; (11bS,11b’S)-2,6-bis(3,4,5-trifluorophenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide; In water; toluene; at 25 ℃; for 20h;

With hydrogenchloride; In water; at 25 ℃; for 18h; Overall yield = 18 %; Overall yield = 69.1 g;

Reference yield:

2-Amino-2-ethyl-hexanoic acid (6300-78-3) → ethyl (S)-2-amino-2-ethylhexanoate (164262-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / Heating

2: 31 percent / porcine liver esterase / aq. phosphate buffer / 7.5 h / 30 °C / pH 8.0

With porcine liver esterase; sulfuric acid; In phosphate buffer; 1: Esterification / 2: Hydrolysis;

DOI:10.1002/1522-2675(20001004)83:10<2823::AID-HLCA2823>3.0.CO;2-#

upstream raw materials:

(+/-)-ethyl 2-amino-2-ethylhexanoate

2-Amino-2-ethyl-hexanoic acid

heptan-3-one

2-amino-2-ethylhexanonitrile

Refernces

• 1、 -. "Hypolipidemic 1,4-benzothiazepine derivative". Page 14-15. . Retrieved 2010/01/31.
• 2、 Liu, Weiguo,Ray, Paul,Benezra, Steven A.. "Chemo-Enzymic Synthesis of Optically Active α,α-Disubstituted α-Amino Acids". . p. 553 - 560. Retrieved 2007/10/02.