Fmoc-l-2-amino-3-(dimethylamino)-propionic acid

Base Information

• Chemical Name: Fmoc-l-2-amino-3-(dimethylamino)-propionic acid
• CAS No.: 587880-86-2
• Molecular Formula: C20H22N2O4
• Molecular Weight: 354.40000
• DSSTox Substance ID: DTXSID40477297
• Nikkaji Number: J1.922.774J
• Wikidata: Q82309704
• Mol file: 587880-86-2.mol

Synonyms:fmoc-l-2-amino-3-(dimethylamino)-propionic acid;587880-86-2;Fmoc-beta-N,N-dimethylamino-L-Ala;(2S)-3-(dimethylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(dimethylamino)propanoic acid;(2s)-3-(Dimethylamino)-2-({[(9h-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;FMOC-AZA-L-LEUCINE;(2S)-3-(dimethylamino)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid;DTXSID40477297;L-Alanine, 3-(dimethylamino)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;CS-0246718;EN300-341836;F83201;Fmoc-beta-N,N-Dimethylamino-L-Ala, AldrichCPR;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(dimethylamino)propanoic acid

Chemical Property of Fmoc-l-2-amino-3-(dimethylamino)-propionic acid

Chemical Property:

• PSA: 78.87000
• LogP: 2.93080
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 354.15795719
• Heavy Atom Count: 26
• Complexity: 488

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-L-2-amino-3-(dimethylamino)-propionicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CN(C)C[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-l-2-amino-3-(dimethylamino)-propionic acid

There total 6 articles about Fmoc-l-2-amino-3-(dimethylamino)-propionic 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:

(S)-2-Benzyloxycarbonylamino-3-dimethylamino-propionic acid; hydrochloride → 3-dimethylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (587880-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / methanol / 1 h

2: 0.96 g / DIEA / acetonitrile; H₂O / 5 h / 20 °C / pH 9

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; water; acetonitrile;

DOI:10.1021/ja029892o

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-Amino-3-dimethylamino-propionic acid; hydrochloride → 3-dimethylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (587880-86-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 20 ℃; for 5h; pH=9;

DOI:10.1021/ja029892o

Reference yield:

C20H20N2O4 → 3-dimethylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (587880-86-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; at 60 ℃; for 8h; regioselective reaction;

DOI:10.1039/c4cc09780g

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid

Refernces

• 1、 Kretsinger, Juliana K.,Schneider, Joel P.. "Design and application of basic amino acids displaying enhanced hydrophobicity". . p. 7907 - 7913. Retrieved 2007/10/03.