N-Benzyloxycarbonyl-beta-alanine

Base Information

• Chemical Name: N-Benzyloxycarbonyl-beta-alanine
• CAS No.: 2304-94-1
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.229
• Hs Code.: 29242990
• European Community (EC) Number: 218-967-4
• NSC Number: 657842,28943,17161
• UNII: 7HUM5U2LG6
• DSSTox Substance ID: DTXSID70177596
• Nikkaji Number: J208.192J
• Wikidata: Q72515281
• Mol file: 2304-94-1.mol

Synonyms:2304-94-1;Z-beta-Ala-OH;carbobenzyloxy-beta-alanine;N-Cbz-beta-alanine;Cbz-beta-alanine;N-Benzyloxycarbonyl-beta-alanine;Cbz-beta-Ala-OH;3-(benzyloxycarbonylamino)propanoic acid;Z-|A-Ala-OH;3-(phenylmethoxycarbonylamino)propanoic acid;3-(((Benzyloxy)carbonyl)amino)propanoic acid;benzyloxycarbonyl-beta-alanine;N-Cbz-.beta.-alanine;3-{[(benzyloxy)carbonyl]amino}propanoic acid;MFCD00037292;N-Carbobenzoxy-beta-alanine;7HUM5U2LG6;N-carbobenzyloxy-beta-alanine;EINECS 218-967-4;NSC-17161;NSC-28943;NSC657842;N-(Benzyloxycarbonyl)-.beta.-alanine;N-[(Benzyloxy)carbonyl]-beta-alanine;NSC-657842;3-(benzyloxycarbonylamino)propionic acid;.Beta.-alanine, N-[(phenylmethoxy)carbonyl]-;Z-beta-alanine;N-Cbz-b-alanine;3-[N-(benzyloxycarbonyl)amino]propionic acid;3-(N-(BENZYLOXYCARBONYL)AMINO)PROPIONIC ACID;.BETA.-ALANINE, N-((PHENYLMETHOXY)CARBONYL)-;Z-betaAla;Z-ss-Alanine;NSC28943;Z-beta-Al-a-OH;n-(cbz)-beta-alanine;Z-b-Ala-OH;Z--Ala-OH;carbobenzoxy-beta-alanine;beta-Alanine, N-[(phenylmethoxy)carbonyl]-;Z-?-Ala-OH;UNII-7HUM5U2LG6;3-(cbz-amino)propanoic acid;SCHEMBL127662;3-(Cbz-amino)-propanoic acid;DTXSID70177596;CARBOBENZOXY-.BETA.-ALANINE;n-[(benzyloxy)carbonyl]beta-alanine;NSC17161;NSC 17161;NSC 28943;3-benzyloxycarbonylaminopropionic acid;N-CARBOBENZOXY-.BETA.-ALANINE;N-CARBOBENZOYL-.BETA.-ALANINE;3-benzyloxycarbonylamino-propionic acid;AKOS000169760;CS-W013095;HY-W012379;N-CARBOBENZYLOXY-.BETA.-ALANINE;N-[(Benzyloxy)carbonyl]-beta-alanine #;AS-10812;SY002078;FT-0634189;EN300-40979;F12383;M03073;.BETA.-ALANINE, N-CARBOXY-, N-BENZYL ESTER;J-300319;N-((PHENYLMETHOXY)CARBONYL)-.BETA.-ALANINE;Q-201943

Chemical Property of N-Benzyloxycarbonyl-beta-alanine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.27E-08mmHg at 25°C
• Melting Point: 100-105 °C
• Refractive Index: 1.546
• Boiling Point: 435.9 °C at 760 mmHg
• PKA: 4.45±0.10(Predicted)
• Flash Point: 217.4 °C
• PSA: 75.63000
• Density: 1.249 g/cm³
• LogP: 1.77840
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

N-Carbobenzoxy-β-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCC(=O)O
• Uses: N-Carbobenzoxy-β-alanine has been utilized for various synthesis applications including palladium-catalyzed asymmetric allylation of?β-diketones, branched linker that can increase the potency of doxorubicin immunoconjugates, and diacridines that intercalate nucleic acids and inhibit DNA synthesis.

Technology Process of N-Benzyloxycarbonyl-beta-alanine

There total 27 articles about N-Benzyloxycarbonyl-beta-alanine 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: 10.0%

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → 3-(benzyloxycarbonylamino)propanoic acid (2304-94-1)

Guidance literature:

With NADH oxidase; horse liver alcohol dehydrogenase; Enzymatic reaction;

DOI:10.1039/c5ra14414k

Reference yield: 7.4%

C18H20N4O4*H(1+) → 3-(benzyloxycarbonylamino)propanoic acid (2304-94-1) + C7H9N3O*H(1+)

Guidance literature:

With L-Phenylalanine amide; sodium chloride; calcium chloride; In N,N-dimethyl-formamide; at 25 ℃; for 3h; pH=8; aq. buffer;

DOI:10.1002/cbic.201100267

Reference yield:

N-carbobenzoxy-β-alanine-p-nitrophenyl ester (3642-91-9) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 3-(benzyloxycarbonylamino)propanoic acid (2304-94-1)

Guidance literature:

With 1H-imidazole; water; In ethanol; at 25 ℃; Mechanism; Kinetics; phosphate buffer (pH=8.05);

upstream raw materials:

N-benzyloxycarbonyl-3-aminopropionic acid methyl ester

benzyl chloroformate

3-amino propanoic acid

succinic acid anhydride

Downstream raw materials:

Z-β-Ala-Gly-Gly-OEt

2-(dimethylamino)ethyl N-(benzyloxycarbonyl)-3-aminopropionate

N-carbobenzoxy-β-alanine-p-nitrophenyl ester

methyl N-(3-(((benzyloxy)carbonyl)amino)propanoyl)-L-alaninate

Refernces

• 1、 -. "GLUCOPYRANOSYL DERIVATIVE AND USE THEREOF". Paragraph 0293-0295. . Retrieved 2020/12/16.
• 2、 Masdeu, Gerard,Pérez-Trujillo, Míriam,López-Santín, Josep,álvaro, Gregorio. "Chloroperoxidase-catalyzed amino alcohol oxidation: Substrate specificity and novel strategy for the synthesis of N-Cbz-3-aminopropanal". . p. 1204 - 1211. Retrieved 2016/08/09.