Cbz-L-2,4-diaminobutyric acid

Base Information

• Chemical Name: Cbz-L-2,4-diaminobutyric acid
• CAS No.: 62234-40-6
• Molecular Formula: C12H16N2O4
• Molecular Weight: 252.27
• Hs Code.: 2924299090
• European Community (EC) Number: 878-964-4
• DSSTox Substance ID: DTXSID30427044
• Nikkaji Number: J1.628.183B
• Mol file: 62234-40-6.mol

Synonyms:62234-40-6;Z-Dab-OH;Cbz-L-2,4-diaminobutyric acid;(S)-4-Amino-2-(((benzyloxy)carbonyl)amino)butanoic acid;(S)-4-amino-2-(benzyloxycarbonylamino)butanoic acid;(S)-4-Amino-2-(Cbz-amino)butanoic Acid;(2S)-4-amino-2-(phenylmethoxycarbonylamino)butanoic acid;(2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoic acid;(2S)-4-azaniumyl-2-(phenylmethoxycarbonylamino)butanoate;BUTANOIC ACID, 4-AMINO-2-[[(PHENYLMETHOXY)CARBONYL]AMINO]-, (2S)-;Z-Dbu-OH;MFCD00077904;Nalpha-Z-L-2,4-diaminobutyric acid;N-ALPHA-CBZ-L-2,4-DIAMINOBUTYRIC ACID;SCHEMBL1023794;DTXSID30427044;KXMSCBRTBLPGIN-JTQLQIEISA-N;FD1079;N-|A-Z-D-2,4-diaminobutyric acid;AKOS005146457;AC-5664;CS-W008247;DS-13389;AM20040886;(S)-4-Amino-2-(carbobenzoxyamino)butyric acid;EN300-6504358;Z-Dab-OH, >=99.0% (sum of enantiomers, TLC);(2S)-2-benzyloxycarbonylamino-4-aminobutanoic acid;(S)-4-Amino-2-(((benzyloxy)carbonyl)amino)butanoicacid;N-ALPHA-BENZYLOXYCARBONYL-L-2,4-DIAMINOBUTYRIC ACID

Chemical Property of Cbz-L-2,4-diaminobutyric acid

Chemical Property:

• Vapor Pressure: 3.77E-10mmHg at 25°C
• Melting Point: 194-196 °C
• Refractive Index: 1.563
• Boiling Point: 480.3 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 244.3 °C
• PSA: 101.65000
• Density: 1.266 g/cm³
• LogP: 1.80600
• Storage Temp.: Store at RT.
• 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:

99% ^*data from raw suppliers

(S)-4-Amino-2-(benzyloxycarbonylamino)butyricAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCN)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CCN)C(=O)O
• Uses: N-alpha-Z-D-2,4-Diaminobutyric Acid

Technology Process of Cbz-L-2,4-diaminobutyric acid

There total 4 articles about Cbz-L-2,4-diaminobutyric 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: 87.0%

Cbz-L-Gln (2650-64-8) → (2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid (62234-40-6)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In tetrahydrofuran; water; at 4 ℃; for 8h;

DOI:10.1081/SCC-120028636

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-2,4-diaminobutyrate (1758-80-1) → (2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid (62234-40-6)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid (62234-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / acetone / 20 °C / pH 8 - 9

2: [bis(acetoxy)iodo]benzene / ethyl acetate; tetrahydrofuran; water / 12 h / 0 - 20 °C

With [bis(acetoxy)iodo]benzene; sodium carbonate; In tetrahydrofuran; water; ethyl acetate; acetone; 2: |Hofmann Rearrangement;

upstream raw materials:

Cbz-L-Gln

N-benzyloxycarbonyl-L-glutamic acid

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide

Downstream raw materials:

Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid

C₂₁H₃₀N₂O₃

2-(benzyloxycarbonylamino)-4-(2'-nitrophenylamino)butanoic acid

L-2,4-diaminobutyrate

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS". Page/Page column 168; 169. . Retrieved 2018/02/28.
• 2、 Long, Bohua,Tang, Shoubin,Chen, Ligong,Qu, Shiwei,Chen, Bo,Liu, Junyang,Maguire, Anita R.,Wang, Zhuo,Liu, Yuqing,Zhang, Hui,Xu, Zhengshuang,Ye, Tao. "Total synthesis of padanamides A and B". supporting information. p. 2977 - 2979. Retrieved 2013/05/22.