diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate

Base Information

• Chemical Name: diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate
• CAS No.: 116387-28-1
• Molecular Formula: C₃₀H₄₁N₅O₇
• Molecular Weight: 583.685
• Mol file: 116387-28-1.mol

Synonyms:diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate

Chemical Property of diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate

There total 23 articles about diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate 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: 100.0%

Diethyl 2-pivaloyl-5,10-dideazafolate (123910-95-2) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate (116387-28-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In trifluoroacetic acid; for 24h; under 2585.7 Torr;

DOI:10.1021/jo00297a044

Reference yield:

diethyl-L-glutamate hydrochloride (1118-89-4) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate (116387-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, phenyl N-phenylphosphoramidochloridate / 1.) ether, THF, RT, 0.5 h, 2.) 8 h

2: 54 percent / triethylamine, palladium chloride, triphenylphosphine, cuprous iodide / acetonitrile / 2.5 h / Heating

3: 100 percent / H₂ / 5percent Pd/C / trifluoroacetic acid / 24.5 h / 2740.9 Torr / Ambient temperature

With copper(l) iodide; hydrogen; triethylamine; triphenylphosphine; Phenyl N-phenylphosphoramidochloridate; palladium dichloride; palladium on activated charcoal; In acetonitrile; trifluoroacetic acid;

DOI:10.1021/jo00276a023

Reference yield:

tert-butyl-4-bromobenzoate (59247-47-1) → diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate (116387-28-1)

Guidance literature:

Multi-step reaction with 6 steps

1: palladium acetate, triphenylphosphine, triethylamine / 16 h / 100 °C

2: K₂CO₃ / methanol / 3 h / Ambient temperature

3: 69 percent / triphenylphosphine, triethylamine, palladium chloride, cuprous iodide / acetonitrile / 2.5 h / Heating

4: 93 percent / HCl (gas) / nitromethane / 1 h / Ambient temperature

5: 1.) N-methylmorpholine, N-methylpyrrolidone, phenyl N-phenylphosphoramidochloridate / 1.) RT, 20 min, 2.) 24 h

6: 100 percent / H₂ / 5percent Pd/C / trifluoroacetic acid / 24.5 h / 2740.9 Torr / Ambient temperature

With 4-methyl-morpholine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; copper(l) iodide; hydrogen; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; Phenyl N-phenylphosphoramidochloridate; palladium dichloride; palladium on activated charcoal; In methanol; nitromethane; acetonitrile; trifluoroacetic acid;

DOI:10.1021/jo00276a023

upstream raw materials:

Diethyl 2-pivaloyl-5,10-dideazafolate

tert-butyl-4-bromobenzoate

4-Ethynyl-benzoic acid

2-pivaloylamino-6-bromo-4(3H)-pyrido[2,3-d]pyrimidinone

Downstream raw materials:

(6RS)-5,10-dideaza-5,6,7,8-tetrahydrofolic acid

Refernces

• 1、 Taylor,Wong. "Convergent and efficient palladium-effected synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)". . p. 3618 - 3624. Retrieved 2007/10/02.