4-(((Benzyloxy)carbonyl)amino)butanoic acid

Base Information

• Chemical Name: 4-(((Benzyloxy)carbonyl)amino)butanoic acid
• CAS No.: 5105-78-2
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• European Community (EC) Number: 875-161-0
• NSC Number: 120007
• UNII: 8LTF87845X
• DSSTox Substance ID: DTXSID10199055
• Nikkaji Number: J77.575D
• Wikidata: Q83071946
• ChEMBL ID: CHEMBL1556967
• Mol file: 5105-78-2.mol

Synonyms:5105-78-2;Z-Gamma-Abu-Oh;4-(((Benzyloxy)carbonyl)amino)butanoic acid;N-Cbz-gaba;Carbobenzoxy-4-aminobutyric acid;N-Cbz-4-aminobutanoic Acid;4-{[(benzyloxy)carbonyl]amino}butanoic acid;Z-GABA-OH;N-Carbobenzoxy-gamma-aminobutyric acid;4-(benzyloxycarbonylamino)butanoic acid;4-(phenylmethoxycarbonylamino)butanoic acid;N-Cbz-4-aminobutyric Acid;4-(Carboxyamino)butyric acid N-benzyl ester;NSC 120007;4-(((Phenylmethoxy)carbonyl)amino)butanoic acid;Butanoic acid, 4-(((phenylmethoxy)carbonyl)amino)-;4-(Benzyloxycarbonylamino)butyric acid;BRN 1884426;N-Carbobenzoxy-4-aminobutyric Acid;MFCD00055835;NSC-120007;BUTYRIC ACID, 4-(CARBOXYAMINO)-, N-BENZYL ESTER;4-06-00-02342 (Beilstein Handbook Reference);4-[[(Phenylmethoxy)carbonyl]amino]butanoic acid;Z-gamma-aminobutyric acid;Cbz-|A-Aminobutyric acid;Z--Abu-OH;Z-|A-Abu-OH;Z-?-Abu-OH;4-[(phenylmethoxy)carbonylamino]butanoic acid;N-Cbz-4-aminobutanoicAcid;Z-Abu(4)-OH;Z- gamma -aminobutyric acid;MLS000080798;SCHEMBL319161;Z-GABA-OH,Z-gama-Abu-OH;Z-4-AMINOBUTANOIC ACID;CHEMBL1556967;DTXSID10199055;8LTF87845X;HMS2406P21;N-carbobenzoxy-g-aminobutyric acid;4-benzyloxycarbonylaminobutyric acid;N-Cbz-.gamma.-amino-n-butyric acid;BBL007560;NSC120007;STK100964;AKOS000163780;4-(N-carbobenzyloxy-amino)butyric acid;CS-W012857;4-[1-(benzyloxy)formamido]butyric acid;N-Carbobenzoxy-.gamma.-aminobutyric acid;4-[(benzyloxycarbonyl)amino]butanoic acid;AS-18001;gamma-(benzyloxycarbonylamino)butyric acid;LS-47895;SMR000035628;SY022559;4-((N-Benzyloxycarbonyl)amino)butyric acid;FT-0662911;EN300-50365;10.14272/STQMDRQJSNKUAW-UHFFFAOYSA-N;4-([(Benzyloxy)carbonyl]amino)butanoic acid #;AB00118672-01;AB00118672-10;N-Carbobenzoxy-4-amino-n-butyric acid (gamma-);10.14272/STQMDRQJSNKUAW-UHFFFAOYSA-N.1;AO-365/40892059;Butyric acid, 4-(carboxyamino)-, 4-benzyl ester;doi:10.14272/STQMDRQJSNKUAW-UHFFFAOYSA-N;SR-01000399403;doi:10.14272/STQMDRQJSNKUAW-UHFFFAOYSA-N.1;GAMMA-N-CARBOBENZOXY-4-AMINO-N-BUTYRIC ACID;J-300323;SR-01000399403-1;Z57100132;Butanoic acid, 4-(((phenylmethoxy)carbonyl)amino)- (9CI)

Chemical Property of 4-(((Benzyloxy)carbonyl)amino)butanoic acid

Chemical Property:

• Vapor Pressure: 4.57E-09mmHg at 25°C
• Melting Point: 64°C
• Boiling Point: 454.9°Cat760mmHg
• PKA: 4.70±0.10(Predicted)
• Flash Point: 228.9°C
• PSA: 75.63000
• Density: 1.215g/cm³
• LogP: 2.16850
• Storage Temp.: Store at RT.
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

Z-γ-aminobutyric acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCCC(=O)O
• Uses: γ-Aminobutyric acid (A602920) derivative. Antineoplastic agent. Suppresses electrical induced seizures.

Technology Process of 4-(((Benzyloxy)carbonyl)amino)butanoic acid

There total 37 articles about 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: 100.0%

4-benzyloxycarbonylaminobutyric acid 2-methoxyethyl ester (1245613-17-5) → 2-methoxy-ethanol (109-86-4,95507-80-5) + 4-(benzyloxycarbonylamino)butyric acid (5105-78-2)

Guidance literature:

With methanol; Bacillus subtilis esterase; In hexane; at 37 ℃; for 0.5h; pH=7.4; Reagent/catalyst; Time; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/adsc.200900325

Reference yield: 100.0%

allyl 4-(benzyloxycarbonylamino)butanoate → 4-(benzyloxycarbonylamino)butyric acid (5105-78-2) + allyl alcohol (107-18-6)

Guidance literature:

With phosphate buffer; Bacillus subtilis esterase BS₂; In methanol; hexane; at 37 ℃; for 0.5h; pH=7.4; Further Variations:; reaction times; enzyme/substrate ratios; Product distribution;

DOI:10.1021/jo061871f

Reference yield: 99.0%

benzyl formate (104-57-4) + 4-amino-n-butyric acid (56-12-2) → 4-(benzyloxycarbonylamino)butyric acid (5105-78-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 4h;

upstream raw materials:

4-amino-n-butyric acid

glutaric anhydride,

benzyl alcohol

benzyl chloroformate

Downstream raw materials:

N-(4-benzyloxycarbonylamino-butyryl)-N'-isonicotinoyl hydrazine

N-hydroxysuccinimide ester of 4-<(carbobenzyloxy)amino>butyric acid

N-cetyl-γ-(carbobenzoxyamino)butyramide

4-Benzyloxycarbonylamino-butyric acid pentadecyl ester

Refernces

• 1、 -. "MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS". Paragraph 0126; 0136-0137. . Retrieved 2021/07/29.
• 2、 Tropmann, Katharina,Bresinsky, Merlin,Forster, Lisa,M?nnich, Denise,Buschauer, Armin,Wittmann, Hans-Joachim,Hübner, Harald,Gmeiner, Peter,Pockes, Steffen,Strasser, Andrea. "Abolishing Dopamine D2long/D3Receptor Affinity of Subtype-Selective Carbamoylguanidine-Type Histamine H2Receptor Agonists". supporting information. p. 8684 - 8709. Retrieved 2021/06/30.