(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid
• CAS No.: 481055-29-2
• Molecular Formula: C20H21F2NO4
• Molecular Weight: 377.388
• DSSTox Substance ID: DTXSID00892366
• Wikidata: Q81987640
• Mol file: 481055-29-2.mol

Synonyms:481055-29-2;(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid;N-{[(1,1-dimethylethyl)oxy]carbonyl}-4-fluoro-beta-(4-fluorophenyl)-L-phenylalanine;N-alpha-t-Butyloxycarbonyl-3,3-di-(p-fluorophenyl)-L-alanine;SCHEMBL3150241;DTXSID00892366;LXUFYGLEWCKTKN-KRWDZBQOSA-N;CS-0368890;N-(tert-butoxycarbonyl)-4-fluoro-beta-(4-fluorophenyl)-L-phenylalanine;(2S)-3,3-bis(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Chemical Property of (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 377.14386448
• Heavy Atom Count: 27
• Complexity: 485

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid

There total 8 articles about (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-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: 95.0%

(2S)-2-amino-3,3-bis(4-fluorophenyl) propanoic acid (481055-28-1) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid (481055-29-2)

Guidance literature:

(2S)-2-amino-3,3-bis(4-fluorophenyl) propanoic acid; di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; for 12h;

With hydrogenchloride; In dichloromethane; water; pH=3;

Reference yield:

L-2-acetylamino-3,3-bis(4-fluorophenyl)propanoic acid (R)-(+)-1-(4-methylphenyl)ethylamine salt + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid (481055-29-2)

Guidance literature:

L-2-acetylamino-3,3-bis(4-fluorophenyl)propanoic acid (R)-(+)-1-(4-methylphenyl)ethylamine salt; With sulfuric acid; In water; ethyl acetate;

With sulfuric acid; In water; tert-butyl alcohol; at 100 ℃; for 14.5h;

di-tert-butyl dicarbonate; With hydrogenchloride; sodium hydroxide; more than 3 stages; Product distribution / selectivity;

Reference yield:

4-fluoro-β-(4-fluorophenyl)-L-phenylalanine hydrochloride (918625-32-8) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid (481055-29-2)

Guidance literature:

4-fluoro-β-(4-fluorophenyl)-L-phenylalanine hydrochloride; di-tert-butyl dicarbonate; With potassium hydroxide; In water; acetone; at 25 ℃; for 1h; pH=9-10; Large scale;

With hydrogenchloride; In water; pH=2.6; Large scale;

DOI:10.1021/op3002855

upstream raw materials:

(2S)-2-amino-3,3-bis(4-fluorophenyl) propanoic acid

di-tert-butyl dicarbonate

4-fluoro-β-(4-fluorophenyl)-L-phenylalanine hydrochloride

4,4'-Difluorobenzophenone

Downstream raw materials:

denagliptin tosylate

tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate