N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE

Base Information

• Chemical Name: N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE
• CAS No.: 10068-52-7
• Molecular Formula: C11H10F3NO4
• Molecular Weight: 277.2
• Hs Code.: 2924299090
• Mol file: 10068-52-7.mol

Synonyms:N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE;3,3,3-Trifluoro-N-[(phenylMethoxy)carbonyl]alanine;2-(((Benzyloxy)carbonyl)amino)-3,3,3-trifluoropropanoic acid

Chemical Property of N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE

Chemical Property:

• PSA: 79.12000
• LogP: 2.13270
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,3,3-Trifluoro-N-[(phenylmethoxy)carbonyl]alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,3,3-Trifluoro-N-[(phenylmethoxy)carbonyl]alanine, can be used for the synthesis of 3,3,3-Trifluoroalanine and of 3,3,3-Trifluoroalanyl peptides.

Technology Process of N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE

There total 6 articles about N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE 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: 71.0%

(2S,3S)-2-benzyloxycarbonyl[N-(toluene-4-thio)amino]-3-trifluoroacetoxy-2-trifluoromethylbutyric acid methyl ester (276862-99-8) → 2-(N-benzyloxycarbonylamino)-3,3,3-trifluoropropionic acid (10068-52-7) + 2-benzyloxycarbonylamino-3,3,3-trifluoropropionic acid methyl ester (27240-49-9) + (2-hydroxy-1-trifluoromethylethyl)carbamic acid benzyl ester (276863-01-5)

Guidance literature:

With potassium carbonate; In water; acetonitrile; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jo991534p

Reference yield: 65.0%

N-benzyloxycarbonyl-1,1,1-trifluoro-4-(p-tolyl)-3-buten-2-amine (817164-27-5) → 2-(N-benzyloxycarbonylamino)-3,3,3-trifluoropropionic acid (10068-52-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; at 20 ℃;

DOI:10.1021/jo048682m

Reference yield: 54.0%

3,3,3-trifluoro-DL-alanine (17463-43-3) + benzyl chloroformate (501-53-1,94274-21-2) → 2-(N-benzyloxycarbonylamino)-3,3,3-trifluoropropionic acid (10068-52-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 5h;

upstream raw materials:

N-(trifluoromethyl-2-propyl)carbamic acid benzyl ester

3,3,3-trifluoro-DL-alanine

benzyl chloroformate

2-benzyloxycarbonylamino-3,3,3-trifluoropropionic acid methyl ester

Downstream raw materials:

3,3,3-Trifluor-N-benzyloxycarbonyl-alanin-tert.-butylester

(-)-(2R)-N-benzyloxycarbonyl-3,3,3-trifluoroalanine

2-benzyloxycarbonylamino-3,3,3-trifluoropropionic acid methyl ester

3,3,3-Trifluor-N-benzyloxycarbonyl-DL-alanyl-glycin-methylester

Refernces

• 1、 -. "POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS". Paragraph 00588. . Retrieved 2017/07/06.
• 2、 Crucianelli, Marcello,Bravo, Pierfrancesco,Arnone, Alberto,Corradi, Eleonora,Meille, Stefano V.,Zanda, Matteo. "The 'non-oxidative' Pummerer reaction: Conclusive evidence for S(N)2- type stereoselectivity, mechanistic insight, and synthesis of enantiopure L- α-trifluoromethylthreoninate and D-α-trifluoromethyl-allo-threoninate". . p. 2965 - 2971. Retrieved 2007/10/03.