N¹⁰-(trifluoroacetyl)pyrofolic acid

Base Information

• Chemical Name: N¹⁰-(trifluoroacetyl)pyrofolic acid
• CAS No.: 223378-68-5
• Molecular Formula: C₂₁H₁₆F₃N₇O₆
• Molecular Weight: 519.397
• Mol file: 223378-68-5.mol

Synonyms:N¹⁰-(trifluoroacetyl)pyrofolic acid

Chemical Property of N¹⁰-(trifluoroacetyl)pyrofolic acid

Chemical Property:

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N¹⁰-(trifluoroacetyl)pyrofolic acid

There total 6 articles about N¹⁰-(trifluoroacetyl)pyrofolic 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:

3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid (138965-46-5) → N10-(trifluoroacetyl)pyrofolic acid (223378-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium / 0 °C

1.2: 1 h / 0 °C

1.3: 79 percent / conc. HCl / 0 °C / pH 1

2.1: 100 percent / diethylamine / palladium tetrakistriphenylphosphine / CH₂Cl₂ / 3 h / 20 °C

3.1: 67 percent / tetramethylguanidine / dimethylsulfoxide / 9 h / 25 °C

4.1: tetrahydrofuran / 10.5 h / 0 - 25 °C

4.2: 123 g / ice / tetrahydrofuran / 3 h / 25 °C

With 1,1,3,3-tetramethylguanidine; sodium; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: Metallation / 1.2: Addition / 1.3: Hydrolysis / 2.1: deallylation / 3.1: Acylation / 4.1: Acylation / 4.2: Hydrolysis;

DOI:10.1021/ja971568j

Reference yield:

N-allyloxycarbonyl α-allyl-L-glutamate (91871-28-2) → N10-(trifluoroacetyl)pyrofolic acid (223378-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / diethylamine / palladium tetrakistriphenylphosphine / CH₂Cl₂ / 3 h / 20 °C

2.1: 67 percent / tetramethylguanidine / dimethylsulfoxide / 9 h / 25 °C

3.1: tetrahydrofuran / 10.5 h / 0 - 25 °C

3.2: 123 g / ice / tetrahydrofuran / 3 h / 25 °C

With 1,1,3,3-tetramethylguanidine; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: deallylation / 2.1: Acylation / 3.1: Acylation / 3.2: Hydrolysis;

DOI:10.1021/ja971568j

Reference yield:

folic acid (59-30-3) + trifluoroacetic anhydride (407-25-0) → N10-(trifluoroacetyl)pyrofolic acid (223378-68-5)

Guidance literature:

folic acid; trifluoroacetic anhydride; In tetrahydrofuran; at 0 - 25 ℃; for 10.5h;

With Methamphetamin; In tetrahydrofuran; at 25 ℃; for 3h;

DOI:10.1021/ja971568j

upstream raw materials:

folic acid

trifluoroacetic anhydride

L-glutamic acid

3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid

Downstream raw materials:

Pyroglutamic acid

N²-(4-(((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)benzoyl)-N⁵-(2-aminoethyl)-L-glutamine

L-methyl folate (γ)

Refernces

• 1、 Luo, Jin,Smith, Michael D.,Lantrip, Douglas A.,Wang, Susan,Fuchs. "Efficient syntheses of pyrofolic acid and pteroyl azide, reagents for the production of carboxyl-differentiated derivatives of folic acid". . p. 10004 - 10013. Retrieved 2007/10/03.