Glutamic acid,N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-

Base Information

• Chemical Name: Glutamic acid,N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-
• CAS No.: 22350-60-3
• Molecular Formula: C20H23 N7 O7
• Molecular Weight: 473.445
• Mol file: 22350-60-3.mol

Synonyms:DL-Glutamicacid, N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-;Glutamic acid,N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-(9CI); Glutamic acid,N-[p-[[(2-amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-,DL- (8CI); (?à)-Folinicacid; DL-N5-Formyltetrahydrofolic acid; dl-Folinic acid

Chemical Property of Glutamic acid,N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-

Chemical Property:

• PSA: 220.10000
• Density: 1.68±0.1 g/cm3(Predicted)
• LogP: 1.56520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Glutamic acid,N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-

There total 27 articles about Glutamic acid,N-[4-[[(2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]- 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:

N-<4-<<2(S)--3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid (142811-49-2) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

2: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

4: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

Reference yield:

2-amino-6<<2'(R)-(benzylamino)-3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone (142811-46-9) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / 1 M aq. NaOH -> pH 9.5 / dioxane / 46 h / Ambient temperature

2: 5.01 g / Dess-Martin periodinane, AcOH / CH₂Cl₂ / 1.17 h / Ambient temperature

3: 2) NaBH₃CN / 1) DMF, 0 deg C, 5 min, 2) DMF, 0 deg C, 1 h

4: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

5: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

7: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; sodium hydroxide; hydrogen; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

Reference yield:

2-amino-6-<<2'(R)--3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone (142811-47-0) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.01 g / Dess-Martin periodinane, AcOH / CH₂Cl₂ / 1.17 h / Ambient temperature

2: 2) NaBH₃CN / 1) DMF, 0 deg C, 5 min, 2) DMF, 0 deg C, 1 h

3: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

4: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

6: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; hydrogen; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

upstream raw materials:

tetrahydrofolic acid

formic acid

chloral

N-methyl-N-phenylformamide

Downstream raw materials:

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

5-formyl-10-methyl-5,6,7,8-tetrahydrofolic acid

Refernces

• 1、 Brockman et al.. "-". . p. 4325. Retrieved 1950.
• 2、 Flynn et al.. "-". . p. 1979,1980,1982. Retrieved 1951.
• 3、 Zakrzewski, Sigmund F.,Sansone, Annette M.. "[187] Preparation of folinic acid (N 5-formyltetrahydro folic acid)". . p. 731 - 733. Retrieved 1971.
• 4、 Brunner, Henri,Rosenboem, Sabine. "Enantioselective catalyses CXXXV [1]. Stereoselective hydrogenation of folic acid and 2-methylquinoxaline with optically active rhodium(I)-phosphane complexes". . p. 1371 - 1382. Retrieved 2007/10/03.
• 5、 Rees,Suckling,Wood. "A simple and effective method for preparation of the 6(R)- and 6(S)-diastereoisomers of 5-formyltetrahydrofolate (leucovorin)". . p. 470 - 472. Retrieved 2007/10/02.