Fmoc-beta-chloro-L-alanine

Base Information

• Chemical Name: Fmoc-beta-chloro-L-alanine
• CAS No.: 212651-52-0
• Molecular Formula: C18H16ClNO4
• Molecular Weight: 345.78
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID101203107
• Mol file: 212651-52-0.mol

Synonyms:Fmoc-beta-chloro-L-alanine;212651-52-0;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-chloropropanoic acid;(2R)-3-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;3-Chloro-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine;(2R)-3-chloro-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;FMOC-ALA(3-CL)-OH;Fmoc-3-Chloro-L-alanine;(2R)-3-chloro-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid;Fmoc-beta-Chloro-L-Ala-OH;DTXSID101203107;MFCD00270534;AKOS015837250;AS-56934;CS-0208002;E70530;EN300-1716619;J-013962

Chemical Property of Fmoc-beta-chloro-L-alanine

Chemical Property:

• Boiling Point: 557.3±45.0 °C(Predicted)
• PKA: 3.12±0.10(Predicted)
• PSA: 75.63000
• Density: 1.360±0.06 g/cm3(Predicted)
• LogP: 3.60800
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 345.0767857
• Heavy Atom Count: 24
• Complexity: 450

Purity/Quality:

98%Min ^*data from raw suppliers

Fmoc-β-chloro-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCl)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CCl)C(=O)O
• Uses: Fmoc-β-chloro-L-alanine is a derivative of L-alanine (A481500). L-Alanine used to make in-vivo measurement of glucose and alanine metabolism in studies of patients with diabetes. L-Alanine is a non-essential amino acid for human development. L-Alanine is one of the 20 amino acids encoded by the genetic code.

Technology Process of Fmoc-beta-chloro-L-alanine

There total 1 articles about Fmoc-beta-chloro-L-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: 78.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + β-chloro-L-alanine hydrochloride (51887-89-9,3157-46-8) → (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-chloropropionic acid (212651-52-0)

Guidance literature:

With sodium hydrogencarbonate; In acetone; at 20 ℃; for 48h;

DOI:10.1039/b103832j

Reference yield:

(2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-chloropropionic acid (212651-52-0) → (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2'-methoxyphenyl)propionic acid tert-butyl ester (381222-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / H₂SO₄ / CH₂Cl₂ / 19 h / 20 °C

2.1: 99 percent / NaI / acetone / 72 h / Heating

3.1: Zn; Me₃SiCl / dimethylformamide / 20 °C

3.2: 31 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C

With chloro-trimethyl-silane; sulfuric acid; sodium iodide; zinc; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b103832j

Reference yield:

(2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-chloropropionic acid (212651-52-0) → (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-nitrophenyl)propionic acid tert-butyl ester (381222-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / H₂SO₄ / CH₂Cl₂ / 19 h / 20 °C

2.1: 99 percent / NaI / acetone / 72 h / Heating

3.1: Zn; Me₃SiCl / dimethylformamide / 20 °C

3.2: 59 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C

With chloro-trimethyl-silane; sulfuric acid; sodium iodide; zinc; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b103832j

upstream raw materials:

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

β-chloro-L-alanine hydrochloride

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4'-methoxyphenyl)propionic acid tert-butyl ester

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(3'-methoxyphenyl)propionic acid tert-butyl ester

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2'-methoxyphenyl)propionic acid tert-butyl ester

Refernces