(3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid

Base Information

• Chemical Name: (3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid
• CAS No.: 868071-17-4
• Molecular Formula: C10H9F3O3
• Molecular Weight: 234.175
• Hs Code.: 2918199090
• Mol file: 868071-17-4.mol

Synonyms:(3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid;

Chemical Property of (3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid

Chemical Property:

• Melting Point: 87 °C
• Boiling Point: 340.4±42.0 °C(Predicted)
• PKA: 4.24±0.10(Predicted)
• PSA: 57.53000
• Density: 1.459 g/cm³
• LogP: 1.48200
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-3-Hydroxy-4-(2,4,5-trifluorophenyl)butanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dexrazoxane intermediate

Technology Process of (3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid

There total 23 articles about (3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid 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: 86.0%

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (769195-26-8) → 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid (868071-17-4)

Guidance literature:

With dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen; In methanol; acetic acid; at 70 ℃; under 3620.13 Torr; Inert atmosphere; Autoclave;

Reference yield: 64.0%

4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid (1256815-03-8) → 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid (868071-17-4)

Guidance literature:

4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid; With triethylamine; B-chlorodiisopinocampheylborane; In dichloromethane; at -60 - 0 ℃; for 2h; Inert atmosphere;

With water; sodium hydroxide; In dichloromethane; pH=10; Inert atmosphere;

With hydrogenchloride; In water; pH=5; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.ejmech.2010.08.002

Reference yield: 48.0%

(S)-(2,4,5-trifluorophenyl)-3-tert-butyldimethylsiloxy-butyric acid methyl ester → 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid (868071-17-4)

Guidance literature:

With hydrogenchloride; In water; acetone; at 55 ℃; for 24h; Industrial scale;

upstream raw materials:

4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid

1-bromo-2,4,5-trifluorobenzene

1-allyl-2,4,5-trifluorobenzene

(S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol

Downstream raw materials:

N-benzyloxy-4-(2,4,5-trifluorophenyl)-3(S)-hydroxybutanamide

(S)-3-hydroxy-N-methoxy-4-(2,4,5-trifluorophenyl)butanamide

(S)-3-hydroxy-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

sitagliptin

Refernces

• 1、 -. "Preparation method of sitagliptin intermediate". . . Retrieved 2017/09/01.
• 2、 -. "SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF". Page/Page column 30-31. . Retrieved 2012/03/26.