(2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid

Base Information

• Chemical Name: (2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid
• CAS No.: 2130-77-0
• Molecular Formula: C12H16N2O4
• Molecular Weight: 252.27
• DSSTox Substance ID: DTXSID00693279
• Nikkaji Number: J2.228.624B
• Wikidata: Q82622319
• Mol file: 2130-77-0.mol

Synonyms:2130-77-0;H-Dab(Z)-OH;(2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid;Butanoic acid, 2-amino-4-[[(phenylmethoxy)carbonyl]amino]-, (S)-;(2S)-2-amino-4-(phenylmethoxycarbonylamino)butanoic acid;(S)-2-Amino-4-(((benzyloxy)carbonyl)amino)butanoic acid;(2S)-2-amino-4-(benzyloxycarbonylamino)butanoic acid;DTXSID00693279;CAA13077;MFCD08275863;N(3)-Z-L-2,4-diaminobutyric acid;AKOS007930169;AKOS015891365;N-gamma-z-L-2,4-Diaminobutyric acid;AS-56348;CS-0343820;P18608;EN300-7093055;(S)-2-Amino-4-[(benzyloxycarbonyl)amino]butanoic acid

Chemical Property of (2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid

Chemical Property:

• Melting Point: 225-227 °C
• Boiling Point: 483.2±45.0 °C(Predicted)
• PKA: 2.25±0.10(Predicted)
• PSA: 105.14000
• Density: 1.266±0.06 g/cm3(Predicted)
• LogP: 1.61950
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 252.11100700
• Heavy Atom Count: 18
• Complexity: 277

Purity/Quality:

98% ^*data from raw suppliers

H-Dab(Z)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NCC[C@@H](C(=O)O)N

Technology Process of (2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid

There total 7 articles about (2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic 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:

L-2,4-diaminobutyrate (1758-80-1) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid (2130-77-0)

Guidance literature:

With sodium hydroxide; copper diacetate; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1055/s-2005-869989

Reference yield:

→ (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid (2130-77-0)

Guidance literature:

With water; sodium hydrogencarbonate; benzyl chloroformate; Reagens 4: CHCl₃;

Reference yield:

(S)-2-amino-4-benzyloxycarbonylamino-butyric acid ; copper (II)-salt → (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid (2130-77-0)

Guidance literature:

With hydrogen sulfide; water;

DOI:10.1021/jo9615007

upstream raw materials:

benzyl chloroformate

L-2,4-diaminobutyric acid monohydrochloride

L-2,4-diaminobutyrate

dibenzyl dicarbonate

Downstream raw materials:

H-L-dab(Z)-OMe*HCl

(S)-2-amino-4-benzyloxycarbonylamino-butyric acid ethyl ester; hydrochloride

(S)-4-benzyloxycarbonylamino-2-(toluene-4-sulfonylamino)-butyric acid

(2S)-N⁴-benzyloxycarbonyl-1,2,4-triaminobutane

Refernces

• 1、 Tian, Zong-Qiang,Brown, Bradley B.,Mack, David P.,Hutton, Craig A.,Bartlett, Paul A.. "Potentially macrocyclic peptidyl boronic acids as chymotrypsin inhibitors". . p. 514 - 522. Retrieved 2007/10/03.