(betaS)-N-Acetyl-beta-methyl-L-phenylalanine

Base Information

• Chemical Name: (betaS)-N-Acetyl-beta-methyl-L-phenylalanine
• CAS No.: 25488-28-2
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.256
• DSSTox Substance ID: DTXSID201281671
• Nikkaji Number: J2.047.480G
• Mol file: 25488-28-2.mol

Synonyms:DTXSID201281671;25488-28-2;(betaS)-N-Acetyl-beta-methyl-L-phenylalanine

Chemical Property of (betaS)-N-Acetyl-beta-methyl-L-phenylalanine

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)C(C(=O)O)NC(=O)C
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)[C@@H](C(=O)O)NC(=O)C

Technology Process of (betaS)-N-Acetyl-beta-methyl-L-phenylalanine

There total 11 articles about (betaS)-N-Acetyl-beta-methyl-L-phenylalanine 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: 83.0%

N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide (145122-93-6) → (2S,3S)-N-acetyl-β-methylphenylalanine (25488-28-2)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1002/hlca.19920750622

Reference yield:

phenyllithium (591-51-5) → (2S,3S)-N-acetyl-β-methylphenylalanine (25488-28-2)

Guidance literature:

Multi-step reaction with 6 steps

2: 1) NaN(TMS)2 / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 30 min.

3: 79 percent / 1 N aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 79 percent / Zn-powder, 1 N aq. HCl, AcOH / 20 h / 25 °C

5: 99 percent / pyridine / 6 h / Ambient temperature

6: 83 percent / 1 M aq. H₂O₂, 1 M aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

With pyridine; hydrogenchloride; lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1002/hlca.19920750622

Reference yield:

(2S,2'S,3'S)-N-(2'-amino-3'-phenylbutanoyl)bornane-10,2-sultam (145122-92-5) → (2S,3S)-N-acetyl-β-methylphenylalanine (25488-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / pyridine / 6 h / Ambient temperature

2: 83 percent / 1 M aq. H₂O₂, 1 M aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

With pyridine; lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1002/hlca.19920750622

upstream raw materials:

(2S,3S)-methylphenylalanine

acetic anhydride

N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide

(2S,3S)-β-Methyl-N-phthaloylphenylalanin-methylester

Downstream raw materials:

(Ξ)-3-(L_s-threo-2-acetylamino-3-phenyl-butyrylamino)-3-thiazol-2-yl-propionic acid methyl ester