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

Base Information

• Chemical Name: (S)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate
• CAS No.: 1872-59-9
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• Hs Code.: 2924299090
• ChEMBL ID: CHEMBL5000655
• DSSTox Substance ID: DTXSID80562393
• Nikkaji Number: J898.330E
• Wikidata: Q82446526
• Mol file: 1872-59-9.mol

Synonyms:1872-59-9;(S)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate;O-tert-Butyl-N-carbobenzoxy-L-serine Methyl Ester;methyl (2S)-3-[(2-methylpropan-2-yl)oxy]-2-(phenylmethoxycarbonylamino)propanoate;MFCD00191072;Z-O-tert.butyl-L-serine methyl ester;CHEMBL5000655;DTXSID80562393;BAA87259;(S)-Methyl2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate;AKOS015911690;AM82235;CS-W012070;HY-W011354;AS-46847;F10710;A880593;Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-L-serinate;(S)-methyl 2-(benzyloxycarbonylamino)-3-tert-butoxypropanoate;O-tert-Butyl-N-carbobenZoxy-L-serine methyl ester (CbZ-L-Ser(tBu)-OMe)

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

Chemical Property:

• Vapor Pressure: 7.59E-08mmHg at 25°C
• Melting Point: 43 °C
• Refractive Index: 6 ° (C=2, EtOH)
• Boiling Point: 437.247 °C at 760 mmHg
• PKA: 10.50±0.46(Predicted)
• Flash Point: 218.239 °C
• PSA: 73.86000
• Density: 1.117 g/cm³
• LogP: 2.66040
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 358

Purity/Quality:

98%,99%, ^*data from raw suppliers

O-tert-Butyl-N-carbobenzoxy-L-serine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OCC(C(=O)OC)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC[C@@H](C(=O)OC)NC(=O)OCC1=CC=CC=C1

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

There total 7 articles about (S)-Methyl 2-(((benzyloxy)carbonyl)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: 87.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + tert-butyl alcohol (75-65-0) → (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate (1872-59-9)

Guidance literature:

With sulfuric acid; magnesium sulfate; In dichloromethane; at 25 ℃; for 18h;

DOI:10.1016/S0040-4039(97)01792-9

Reference yield: 66.0%

t-butyl bromide (507-19-7) + N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate (1872-59-9)

Guidance literature:

With zinc trifluoromethanesulfonate; zinc; In toluene; at 25 ℃; for 12h; Sealed tube; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.orglett.0c04206

Reference yield: 57.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + isobutene (115-11-7,15220-85-6) → (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate (1872-59-9)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.07.086

upstream raw materials:

diazomethane

N-benzyloxycarbonyl-O-t-butyl-L-serine

N-benzyloxycarbonyl-L-serine methyl ester

isobutene

Downstream raw materials:

(S)-benzyl (1-(tert-butoxy)-3-oxopropan-2-yl)carbamate

methyl N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-serinate

(S)-O-tert-butylserine

β--propionsaeure

Refernces

• 1、 Kher, Samir S.,Penzo, Maria,Fulle, Simone,Finn, Paul W.,Blackman, Michael J.,Jirgensons, Aigars. "Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1". supporting information. p. 4486 - 4489. Retrieved 2015/02/19.
• 2、 Wright, Stephen W.,Hageman, David L.,Wright, Ann S.,McClure, Lester D.. "Convenient preparations of t-butyl esters and ethers from t-butanol". . p. 7345 - 7348. Retrieved 2007/10/03.