Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid Chemical Properties

Melting point:

136-138℃

Boiling point:

443.1±45.0 °C(Predicted)

Density 

1.292±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

4.30±0.10(Predicted)

form 

Solid

color 

White to Off-White

optical activity

25.305°(C=0.01g/ mI, CHCL3 , 20°C, 589nm)

InChI

InChI=1/C15H18F3NO4/c1-15(2,3)23-14(22)19-9(6-13(20)21)4-8-5-11(17)12(18)7-10(8)16/h5,7,9H,4,6H2,1-3H3,(H,19,22)(H,20,21)/t9-/s3

InChIKey

TUAXCHGULMWHIO-DJEYLCQNNA-N

SMILES

C(C1C=C(F)C(F)=CC=1F)[C@H](CC(=O)O)NC(=O)OC(C)(C)C |&1:10,r|

Safety Information

HazardClass 

IRRITANT

Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid Usage And Synthesis

Physical Form

White to Yellow Solid

Description

Boc-(R) -3-amino-4 -(2,4, 5-trifluorophenyl) butyric acid is an important intermediate for the preparation of sitagliptin. Sitagliptinphosphate is the first dipeptidase -IV(dpp-4) inhibitor approved by FDA in 2006. It is used for the treatment of type II diabetes mellitus. It has obvious hypoglycemic effect when used alone or in combination with metformin and pioglitazone, and it is safe to take, well tolerated, with few adverse reactions.

Uses

(R)-3-((tert-Butoxycarbonyl)amino)-4-(2,4,5-trifluorophenyl)butanoic Acid has been used as a reactant for the preparation of dipeptidyl peptidase-4 (DPP4) inhibitors for the treatment of type 2 diabetes, such as sitagliptin.

Synthesis

(R)-β-tert-butoxycarbonylamino-2,4,5-trifluorophenylbutyric acid ethyl ester could used as a starting material and followed by adding Methanol and LiOHH2O as reaction reagents. Adding dichloromethane to the concentrate and adjust the pH to 2 with 2N HCl. Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid could be obtained through further purification.

Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid(486460-00-8)Related Product Information

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• ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate