(S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid
• CAS No.: 49759-64-0
• Molecular Formula: C17H16FNO4
• Molecular Weight: 317.31
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20559580
• Wikidata: Q82442336
• Mol file: 49759-64-0.mol

Synonyms:49759-64-0;(S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid;Cbz-3-fluoro-L-Phe;(2S)-3-(3-fluorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3-fluorophenyl)propanoic acid;Cbz-3-Fluoro-L-Phenylalanine;Z-Phe(3-F)-OH;N-alpha-Carbobenzoxy-3-fluoro-L-phenylalanine;SCHEMBL7480565;L-Phenylalanine, 3-fluoro-N-[(phenylmethoxy)carbonyl]-;DTXSID20559580;CS-0304770;EN300-12577222;N-[(Benzyloxy)carbonyl]-3-fluoro-L-phenylalanine;(S)-2-(benzyloxycarbonylamino)-3-(3-fluorophenyl)propanoic acid

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid

Chemical Property:

• PSA: 75.63000
• LogP: 3.13870
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 317.10633615
• Heavy Atom Count: 23
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CC(=CC=C2)F)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CC2=CC(=CC=C2)F)C(=O)O

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic acid

There total 7 articles about (S)-2-(((Benzyloxy)carbonyl)amino)-3-(3-fluorophenyl)propanoic 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:

L-3-fluorophenylalanine (19883-77-3,2629-54-1) + benzyl chloroformate (501-53-1,94274-21-2) → Cbz-L-m-FPhe (49759-64-0)

Guidance literature:

DOI:10.1039/b004183l

Reference yield:

Z-DL-Phe(3F)-OCH2CF3 (127862-80-0) → (R)-2-Benzyloxycarbonylamino-3-(3-fluoro-phenyl)-propionic acid (49759-64-0,49759-66-2,126693-47-8)

Guidance literature:

With sodium hydroxide; phosphate buffer; at 25 ℃; for 47h; Yield given. Yields of byproduct given; porcine pancreatic lipase, pH=7.0;

Reference yield:

2-benzyloxycarbonylaminomalonic acid dimethyl ester (37447-35-1) → Cbz-L-m-FPhe (49759-64-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOEt, EtOH

2: aq. KOH, EtOH

3: dioxane / Heating

4: (enzymatic hydrolysis)

With potassium hydroxide; ethanol; sodium ethanolate; In 1,4-dioxane;

DOI:10.1002/hlca.19730560603

upstream raw materials:

Z-DL-Phe(3F)-OMe

L-3-fluorophenylalanine

benzyl chloroformate

2-benzyloxycarbonylaminomalonic acid dimethyl ester

Downstream raw materials:

(3S,4S)-3-{N-benzyloxycarbonyl-β-(3-fluorophenyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one

L-m-FPhe-L-Ala-L-Ala

L-m-FPhe-L-Ala

L-3-fluorophenylalanine