N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenyl Alanine

Base Information

• Chemical Name: N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenyl Alanine
• CAS No.: 105746-37-0
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.428
• Mol file: 105746-37-0.mol

Synonyms:

Chemical Property of N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenyl Alanine

Chemical Property:

• Melting Point: 128 - 129 °C
• Boiling Point: 527.6±39.0 °C(Predicted)
• PKA: 3.61±0.10(Predicted)
• PSA: 66.40000
• Density: 1.104±0.06 g/cm3(Predicted)
• LogP: 3.65180

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenyl Alanine

There total 8 articles about N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenyl Alanine 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: 83.3%

→ nateglinide (105746-37-0,105816-05-5)

Guidance literature:

Purification / work up;

Reference yield: 71.5%

trans-4-isopropylcyclohexyl pivalic anhydride + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → nateglinide (105746-37-0,105816-05-5)

Guidance literature:

trans-4-isopropylcyclohexyl pivalic anhydride; D-(R)-phenylalanine; In water; acetone; at 20 - 30 ℃; for 0.5h; pH=11.5 - 12.5;

With hydrogenchloride; In water; pH=1 - 2; Product distribution / selectivity;

upstream raw materials:

D-(R)-phenylalanine

Refernces

• 1、 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.
• 2、 -. "PROCESS FOR PRODUCTION OF CARBOXYLIC ACID CHLORIDE COMPOUND". Page/Page column 8. . Retrieved 2009/01/24.