(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid

Base Information

• Chemical Name: (S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid
• CAS No.: 83509-88-0
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50453082
• Nikkaji Number: J1.374.265K
• Wikidata: Q82274071
• Mol file: 83509-88-0.mol

Synonyms:83509-88-0;(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid;(3S)-3-(phenylmethoxycarbonylamino)butanoic acid;(S)-3-(CBZ-AMINO)BUTANOIC ACID;(3S)-3-{[(Benzyloxy)carbonyl]amino}butanoic acid;(S)-3-(Cbz-amino)butyric Acid;Cbz-L-3-Aminobutyric acid;Z--HOMOALA-OH;MFCD08277048;(3S)-3-(Benzyloxycarbonylamino)butanoic acid;(S)-3-(((Benzyloxy)carbonyl)amino)butanoicacid;SCHEMBL5194569;DTXSID50453082;AS-37874;Z-beta-Homoala-OH, >=98.0% (HPLC);CS-0095471;EN300-816816;A915156

Chemical Property of (S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid

Chemical Property:

• Melting Point: 105-107 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 435.6±38.0 °C(Predicted)
• PKA: 4.42±0.10(Predicted)
• PSA: 79.12000
• Density: 1.213±0.06 g/cm3(Predicted)
• LogP: 1.98040
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

99% ^*data from raw suppliers

Z-β-Homoala-OH ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid

There total 16 articles about (S)-3-(((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: 98.0%

L-3-aminobutyric acid (3775-72-2) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-3-benzyloxycarbonylaminobutyric acid (83509-88-0)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/S0960-894X(97)00036-X

Reference yield: 98.0%

(S)-2-(N-benzyloxyacarbonylamino)-propyl cyanide → (S)-3-benzyloxycarbonylaminobutyric acid (83509-88-0)

Guidance literature:

With NIT-107 nitrilase; water; at 30 ℃; for 18h; enantioselective reaction; aq. phosphate buffer;

DOI:10.1016/j.tetasy.2009.07.045

Reference yield: 96.0%

benzyl (S)-(4-diazo-3-oxobutan-2-yl)carbamate (67865-68-3,28094-68-0) → (S)-3-benzyloxycarbonylaminobutyric acid (83509-88-0)

Guidance literature:

With silver trifluoroacetate; silica gel; In ethyl acetate; at 50 ℃; for 0.25h;

DOI:10.1080/00397910500290466

upstream raw materials:

benzyl (S)-(4-diazo-3-oxobutan-2-yl)carbamate

methyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate

ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate

L-3-aminobutyric acid

Downstream raw materials:

(S)-3-[(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyrylamino]-butyric acid

(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid 2,4,5-trichloro-phenyl ester

(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid

(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid methyl ester

Refernces

• 1、 Pinho, Vagner D.,Gutmann, Bernhard,Kappe, C. Oliver. "Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation". . p. 37419 - 37422. Retrieved 2014/12/09.
• 2、 Sleebs, Brad E.,Nguyen, Nghi H.,Hughes, Andrew B.. "A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction". . p. 747 - 751. Retrieved 2013/05/08.