(S)-Sitagliptin Phosphate

Base Information

• Chemical Name: (S)-Sitagliptin Phosphate
• CAS No.: 823817-58-9
• Molecular Formula: C16H15F6N5O.H3O4P
• Molecular Weight: 505.314
• UNII: S6NJT48LNH
• Mol file: 823817-58-9.mol

Synonyms:(S)-Sitagliptin Phosphate;823817-58-9;ent-Sitagliptin Phosphate;(S)-Sitagliptin (phosphate);(3S)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric acid;S6NJT48LNH;SCHEMBL1933943;BCP20727;HY-13749C;AKOS040758370;Sitagliptin phosphate anhydrous, (S)-;CS-0018784;(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 phosphate;(S)-3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one phosphate;1,2,4-Triazolo[4,3-a]pyrazine, 7-[(3S)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-, phosphate (1:1);7-[(3S)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine phosphate (1:1)

Chemical Property of (S)-Sitagliptin Phosphate

Chemical Property:

• Melting Point: 193-195°C
• PSA: 164.61000
• LogP: 1.72610
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 4
• Exact Mass: 505.09497466
• Heavy Atom Count: 33
• Complexity: 616

Purity/Quality:

99% ^*data from raw suppliers

ent-Sitagliptin-d4Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
• Isomeric SMILES: C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@H](CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
• Uses: Labelled ent-Sitagliptin Phosphate (S491025). ent-Sitagliptin Phosphate is the S-isomer of Sitagliptin Phosphate (S491000), as an impurity. ent-Sitagliptin Phosphate (Sitagliptin EP Impurity A) is the S-isomer of Sitagliptin Phosphate (S491000), as an impurity.

Technology Process of (S)-Sitagliptin Phosphate

There total 3 articles about (S)-Sitagliptin Phosphate 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: 66.0%

sitagliptin (486460-32-6,823817-55-6) → (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 dihydrogenphosphate salt (823817-58-9,654671-78-0,790712-60-6)

Guidance literature:

With phosphoric acid; In water; at 45 - 75 ℃; Product distribution / selectivity;

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) → sitagliptin phosphate (654671-78-0,790712-60-6) + (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 dihydrogenphosphate salt (823817-58-9,654671-78-0,790712-60-6)

Guidance literature:

With phosphoric acid; In water; isopropyl alcohol; at 20 - 50 ℃; Product distribution / selectivity;

Reference yield:

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 (823817-57-8,654671-78-0,790712-60-6) → sitagliptin phosphate (654671-78-0,790712-60-6) + (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 dihydrogenphosphate salt (823817-58-9,654671-78-0,790712-60-6)

Guidance literature:

In water; isopropyl alcohol; at 20 - 70 ℃; Product distribution / selectivity;

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

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

sitagliptin

Downstream raw materials:

sitagliptin

Sitagliptin hydrochloride

c

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.