(S)-(+)-O-acetylmandelic acid (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

Base Information

• Chemical Name: (S)-(+)-O-acetylmandelic acid (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
• CAS No.: 1219440-29-5
• Molecular Formula: C₁₀H₁₀O₄*C₁₆H₁₅F₆N₅O
• Molecular Weight: 601.505
• Mol file: 1219440-29-5.mol

Synonyms:(S)-(+)-O-acetylmandelic acid (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

Chemical Property of (S)-(+)-O-acetylmandelic acid (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-O-acetylmandelic acid (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

There total 7 articles about (S)-(+)-O-acetylmandelic acid (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 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:

(R/S)-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 (823817-56-7,823817-55-6) + (S)-acetylmandelic acid (7322-88-5) → (S)-(+)-O-acetylmandelic acid (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 (1219440-29-5) + (S)-(+)-O-acetylmandelic acid (2S)-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 (1219440-30-8)

Guidance literature:

In isopropyl alcohol; at 60 - 65 ℃; for 1h;

Reference yield:

(2,4,5-trifluorophenyl)acetic acid (209995-38-0) → (S)-(+)-O-acetylmandelic acid (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 (1219440-29-5) + (S)-(+)-O-acetylmandelic acid (2S)-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 (1219440-30-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap / acetonitrile / 25 - 30 °C

1.2: 30 - 50 °C

2.1: ammonium hydroxide; ammonium acetate; acetic acid / water; methanol / 6 h / 60 - 65 °C

3.1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C

4.1: water / 17 h / 60 - 65 °C

With ammonium hydroxide; methanesulfonic acid; dimethylsulfide borane complex; ammonium acetate; acetic acid; dmap; In tetrahydrofuran; methanol; water; isopropyl alcohol; acetonitrile;

Reference yield:

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride → (S)-(+)-O-acetylmandelic acid (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 (1219440-29-5) + (S)-(+)-O-acetylmandelic acid (2S)-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 (1219440-30-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap / acetonitrile / 25 - 30 °C

1.2: 30 - 50 °C

2.1: ammonium hydroxide; ammonium acetate; acetic acid / water; methanol / 6 h / 60 - 65 °C

3.1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C

4.1: water / 17 h / 60 - 65 °C

With ammonium hydroxide; methanesulfonic acid; dimethylsulfide borane complex; ammonium acetate; acetic acid; dmap; In tetrahydrofuran; methanol; water; isopropyl alcohol; acetonitrile;

upstream raw materials:

(R/S)-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

(S)-acetylmandelic acid

(2,4,5-trifluorophenyl)acetic acid

(S)-Sitagliptin

Refernces

• 1、 -. "IMPROVED PROCESS FOR PREPARATION OF (2R)-4-OXO-4-[3- (TRIFLUOROMETHYL)-5,6-DIHYDRO [1,2,4]-TRIAZOLO[4,3-A]PYRAZIN- 7(8H)-YL]-L-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE and NEW IMPURITIES IN PREPARATION THEREOF". Page/Page column 53. . Retrieved 2010/04/25.