(S)-Methyl 2-amino-3-(tert-butoxy)propanoate

Base Information

• Chemical Name: (S)-Methyl 2-amino-3-(tert-butoxy)propanoate
• CAS No.: 17083-26-0
• Molecular Formula: C8H17 N O3
• Molecular Weight: 175.228
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID90427040
• Nikkaji Number: J510.744J
• Wikidata: Q82239799
• Mol file: 17083-26-0.mol

Synonyms:17083-26-0;(S)-Methyl 2-amino-3-(tert-butoxy)propanoate;methyl (2S)-2-amino-3-[(2-methylpropan-2-yl)oxy]propanoate;O-(tert-Butyl)-L-serine Methyl Ester;METHYL (2S)-2-AMINO-3-(TERT-BUTOXY)PROPANOATE;H-Ser(But)-OMe;methyl O-t-butyl-serinate;methyl O-tert-butyl-L-serinate;SCHEMBL1588396;O-tert-Butylserine methyl ester;MMJPLCPGTJXFNH-LURJTMIESA-;DTXSID90427040;MMJPLCPGTJXFNH-LURJTMIESA-N;Methyl O-(tert-butyl)-L-serinate;AKOS006283461;(S)-methyl 2-amino-3-tert-butoxypropanoate;CS-0448428;(S)-Methyl2-amino-3-(tert-butoxy)propanoate;EN300-4274846;InChI=1/C8H17NO3/c1-8(2,3)12-5-6(9)7(10)11-4/h6H,5,9H2,1-4H3/t6-/m0/s1

Chemical Property of (S)-Methyl 2-amino-3-(tert-butoxy)propanoate

Chemical Property:

• Boiling Point: 43 °C(Press: 0.2 Torr)
• PKA: 6.16±0.33(Predicted)
• PSA: 61.55000
• Density: 1.003±0.06 g/cm3(Predicted)
• LogP: 1.80410
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 175.12084340
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

98% ^*data from raw suppliers

(S)-Methyl2-amino-3-(tert-butoxy)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-Methyl 2-amino-3-(tert-butoxy)propanoate

There total 8 articles about (S)-Methyl 2-amino-3-(tert-butoxy)propanoate 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: 75.0%

methyl N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-serinate (174363-87-2) → O-tert-butyl-L-serine methyl ester (17083-26-0)

Guidance literature:

With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate; In 1,4-dioxane; water; at 80 - 82 ℃; for 4.5h;

DOI:10.1039/c4ra13419b

Reference yield:

(S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate (1872-59-9) → O-tert-butyl-L-serine methyl ester (17083-26-0)

Guidance literature:

With cyclohexene; palladium on activated charcoal; In ethanol; Heating;

DOI:10.1055/s-1976-24159

Reference yield:

acetic acid tert-butyl ester (540-88-5) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → O-tert-butyl-L-serine methyl ester (17083-26-0)

Guidance literature:

With perchloric acid; sulfuric acid; at 20 ℃; for 4h;

upstream raw materials:

(R)-methyl 2-(benzyloxycarbonylamino)-3-t-butoxypropanoate

(S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

isobutene

Downstream raw materials:

Z-Leu-Ser(Bu-t)-OMe

C₁₉H₂₈ClN₃O₆

Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether

methyl (2S)-2-anilino-3-tert-butoxypropanoate

Refernces

• 1、 Majumdar, Swapan,De, Jhinuk,Chakraborty, Ankita,Roy, Dipanwita,Maiti, Dilip K.. "A protic ionic liquid catalyzed strategy for selective hydrolytic cleavage of tert-butyloxycarbonyl amine (N-Boc)". . p. 3200 - 3205. Retrieved 2015/02/03.
• 2、 Yoon, Cheol H.,Flanigan, David L.,Yoo, Kyung S.,Jung, Kyung W.. "Stereogenic evolution of clasto-lactacystin β-lactone from L-serine". . p. 37 - 39. Retrieved 2007/10/03.