922178-94-7

Basic information

• Product Name: BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID
• Synonyms: (S)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid;3-aMino-5-(tert-butoxy)-5-oxo-4-(2,4,5-trifluorophenyl)pentanoic acid;Boc-(S)-3-aMino-4-(2,4,5-rifluoro-phenyl)-butyric acid;(S)-3-(Boc-aMino)-4-(2,4,5-trifluorophenyl)butanoic acid;(S)-Sitagliptin N-Boc-Acid IMpurity;(S)-N-Boc-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid;(3S)-3-{[(tert-Butoxy)carbonyl]amino}-4-(2,4,5-trifluorophenyl)butanoic acid;Boc-(S)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid≥ 98% (HPLC)
• CAS NO: 922178-94-7
• Molecular Formula: C15H18F3NO4
• Molecular Weight: 333.3
• Product Categories: B-Amino
• Mol File: 922178-94-7.mol
• Article Data: 62

Chemical Properties

• Boiling Point: 443.1 °C at 760 mmHg
• Flash Point: 221.8 °C
• Appearance: /
• Density: 1.292
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.30±0.10(Predicted)
• CAS DataBase Reference: BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID(922178-94-7)
• EPA Substance Registry System: BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID(922178-94-7)

Safety Data

• Hazardous Substances Data: 922178-94-7(Hazardous Substances Data)

Usage

Description

BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID is a white powder chemical compound that serves as a crucial reactant in the synthesis of peptidase IV inhibitors. Its unique structure, featuring a trifluorophenyl group and a protected amino group, makes it a valuable intermediate in the development of pharmaceuticals targeting specific enzymatic pathways.

Uses

Used in Pharmaceutical Industry:
BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID is used as a key reactant for the preparation of peptidase IV inhibitors, which are important in the development of medications for the treatment of type 2 diabetes and other metabolic disorders. Peptidase IV inhibitors help regulate the digestion and absorption of carbohydrates, thereby managing blood sugar levels effectively.
As a chemical intermediate, BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID plays a significant role in the synthesis of bioactive molecules, contributing to advancements in medicinal chemistry and drug discovery. Its specific properties allow for targeted modifications and enhancements of peptidase IV inhibitors, potentially leading to more effective treatments and improved patient outcomes.

Upstream product

• 486460-25-7 [3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 
• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 881995-73-9 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 
• 769195-26-8 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester 
• 881995-69-3 (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 764667-64-3 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 157911-56-3 2,4,5-trifluorobenzyl bromide 
• 486460-08-6 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate 
• 486460-07-5 (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine 
• 486460-09-7 (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid 
• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 1152439-73-0 2,2-dimethyl-5-[2-(2,4,5-trifluorophenyl)acetyl]-[1,3]dioxane-4,6-dione 

Downstream Products

• 486459-71-6 (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 
• 1364122-93-9 (R)-4-(3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-7-methoxy-4,5-dihydro-1H-benzo[e][1,4]diazipin-2(3H)-one hydrochloride 
• 1364122-98-4 (R)-4-(3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-8-fluoro-4,5-dihydro-1H-benzo[e][1,4]diazipin-2(3H)-one hydrochloride 
• 1395397-56-4 C₂₇H₂₉F₆N₃O₄ 
• 1395398-00-1 C₂₈H₃₀F₃N₃O₄S 
• 1395398-15-8 C₃₁H₃₂F₄N₄O₄ 
• 1395398-21-6 C₂₅H₂₇F₅N₄O₄ 
• 1395398-18-1 C₂₅H₂₈F₄N₄O₄ 
• 1395397-13-3 C₂₇H₃₄F₃N₃O₄ 
• 1395395-57-9 C₂₂H₂₆F₃N₃O₂ 
• 1395397-52-0 C₂₇H₂₉F₆N₃O₅ 
• 910551-58-5 C₂₆H₃₁F₃N₄O₆S 
• 910550-48-0 t-butyl [(2R)-4-[4-(4-carboxybenzoyl)-1-piperazinyl]-1-(2,4,5-trifluorophenyl)-4-oxobutyl]carbamate 
• 910550-98-0 C₂₇H₃₀F₃N₃O₆ 

Relevant articles and documents

Nickel-Catalyzed Asymmetric Hydrogenation for the Synthesis of a Key Intermediate of Sitagliptin

Nickel-catalyzed enantioselective hydrogenation of enamines leading to the efficient synthesis of 3-R-Boc-amino-4-(2,4,5-trifluorophenyl)butyric esters, the key intermediate of the blockbuster antidiabetic drug (R)-SITAGLIPTIN, is described. The sitagliptin motifs were isolated in more than 99% yield and with 75–92% ee using the earth-abundant nickel catalyst. Upon chiral resolution with (R)- and (S)-1-phenylethylamines, the partially enantioenriched (R)- and (S)-Boc-3-amino-4-(2,4,5-trifluorophenyl)butanoic acids provided >99.5% ee of the crucial sitagliptin intermediate. The asymmetric hydrogenation protocol was scaled up to 10 g with consistency in yield and ee, and has been reproduced in multiple batches.

Synthesis of (?)-(R)-Sitagliptin by RhI-Catalyzed Asymmetric Hydroamination

We report of a concise synthesis of (R)-sitagliptin monophosphate – a drug predominantly applied in the treatment of type 2 diabetes. Utilizing our recently developed RhI-catalyzed hydroamination of allenes for the stereoselective construction of the inherent chiral amino function, a new approach to (R)-sitagliptin monophosphate on a 3.5 mmol scale was established.

Preparation method of 1-morpholinyl-4-(2,4,5-trifluorophenyl)butane-1,3-dione

The invention discloses a preparation method of 1-morpholinyl-4-(2,4,5-trifluorophenyl)butane-1,3-dione, and belongs to the technical field of organic synthesis. The preparation method comprises the following step: under the action of a metal chelating agent and an alkali, carrying out a reaction of the following formula on a compound 2 and a compound 3 in an organic solvent to obtain a compound 1. The preparation method disclosed by the invention is high in yield, simple in post-treatment, simple, feasible, mild in reaction condition and suitable for industrial production.