L-Nateglinide

Base Information

• Chemical Name: L-Nateglinide
• CAS No.: 105816-05-5
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.428
• Hs Code.: 2924296000
• Mol file: 105816-05-5.mol

Synonyms:L-Phenylalanine,N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-, trans-; L-Nateglinide

Chemical Property of L-Nateglinide

Chemical Property:

• Melting Point: 103-111°C
• PSA: 66.40000
• LogP: 3.65180
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

ent-Nateglinide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An impurity found within the commercial pharmaceutical Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent. An impurity found within the commercial pharmaceutical Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent. Nateglinide USP Related Compound B An impurity found within the commercial pharmaceutical Nateglinide (N379375), a common antidiabetic

Technology Process of L-Nateglinide

There total 41 articles about L-Nateglinide 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: 97.0%

N-(trans-4-isopropylcyclohexyl-1-carbonyl)-d-phenylalanine methyl ester → nateglinide (105746-37-0,105816-05-5)

Guidance literature:

N-(trans-4-isopropylcyclohexyl-1-carbonyl)-d-phenylalanine methyl ester; With potassium hydroxide; water; Aliquat 336; In toluene; at 45 - 50 ℃; for 5h;

With hydrogenchloride; In water; at 15 - 20 ℃; pH=2.5; Product distribution / selectivity;

Reference yield: 94.4%

nateglinide methyl ester → N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (105816-05-5)

Guidance literature:

nateglinide methyl ester; With methanol; sodium hydroxide; water; at 20 - 25 ℃; for 4h;

With hydrogenchloride; In water; at 10 - 18 ℃; for 0.5h;

Reference yield: 80.8%

N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester (105746-47-2) → nateglinide (105816-04-4,105816-05-5)

Guidance literature:

N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester; With water; sodium hydroxide; In methanol; at 25 - 30 ℃; for 5h;

With hydrogenchloride; In water; pH=2.0 - 2.5;

upstream raw materials:

N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester

trans-4-isopropylcyclohexane-1-carboxylic acid

D-(R)-phenylalanine

chloroformic acid ethyl ester

Refernces

• 1、 -. "A high-purity process for the preparation of nateglinide". Paragraph 0028; 0030-0032. . Retrieved 2017/05/04.
• 2、 Kaur, Jatinder,Bhardwaj, Atul,Huang, Zhangjian,Narang, Deepak,Chen, Ting-Yueh,Plane, Frances,Knaus, Edward E.. "Synthesis and biological investigations of nitric oxide releasing nateglinide and meglitinide type II antidiabetic prodrugs: In-vivo antihyperglycemic activities and blood pressure lowering studies". . p. 7883 - 7891. Retrieved 2012/11/07.