Sitagliptin N-Boc IMpurity

Base Information

• Chemical Name: Sitagliptin N-Boc IMpurity
• CAS No.: 486460-23-5
• Molecular Formula: C21H23F6N5O3
• Molecular Weight: 507.436
• Mol file: 486460-23-5.mol

Synonyms:N-Boc-Sitagliptin;

Chemical Property of Sitagliptin N-Boc IMpurity

Chemical Property:

• Melting Point: 188-191 °C(Solv: toluene (108-88-3))
• PKA: 11.60±0.46(Predicted)
• PSA: 92.84000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 3.72480
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

N-Boc-Sitagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-Sitagliptin is the N-Boc protected derivative of Sitagliptin (S490990), a dipeptidyl peptidase-4 inhibitor that is used for glycemic control for patients with type 2 diabetes.

Technology Process of Sitagliptin N-Boc IMpurity

There total 105 articles about Sitagliptin N-Boc IMpurity 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: 99.6%

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7) + 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (762240-92-6) → (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate (486460-23-5)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 55 - 60 ℃; for 12h;

Reference yield: 99.0%

3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (486460-21-3) + (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7) → (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate (486460-23-5)

Guidance literature:

With (2-iodo-5-methoxyphenyl)boronic acid; 4-(dimethylamino)pyridine N-oxide; In fluorobenzene; for 40h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c5sc03761a

Reference yield: 95.0%

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride + (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (486460-00-8,922178-94-7) → (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate (486460-23-5)

Guidance literature:

With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 0 - 20 ℃; for 16h;

upstream raw materials:

3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

di-tert-butyl dicarbonate

2,4,5-trifluorobenzyl bromide

Downstream raw materials:

(2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine hydrochloride

sitagliptin phosphate

(2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine phosphate

(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

Refernces

• 1、 -. "Synthesis method of sitagliptin free alkali". Paragraph 0024; 0042-0053; 0060-0069. . Retrieved 2021/07/17.
• 2、 -. "Preparation method of chiral 4 - aryl - β β-amino acid derivative". Paragraph 0059-0061. . Retrieved 2021/11/14.