Methoxycarbonyl-L-tert-leucine

Base Information

• Chemical Name: Methoxycarbonyl-L-tert-leucine
• CAS No.: 162537-11-3
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2933399090
• Mol file: 162537-11-3.mol

Synonyms:N-(Methoxycarbonyl)-L-tert-leucine;(S)-N-(methoxycarbonyl)-tert-leucine;

Chemical Property of Methoxycarbonyl-L-tert-leucine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Melting Point: 109 °C
• Refractive Index: 1.459
• Boiling Point: 320.9 °C at 760 mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: 147.9 °C
• PSA: 75.63000
• Density: 1.126 g/cm³
• LogP: 1.23260
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethyl acetate and methanol.
• Water Solubility.: 26.4g/L at 20℃

Purity/Quality:

99% ^*data from raw suppliers

Methoxycarbonyl-L-tert-leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Methoxycarbonyl-L-tert-leucine is a kind of amino acid deriviative. It is a very useful intermediate for efficient synthesis of the HIV protease inhibitor BMS-232632 as well as atazanavir bisulfate.
• Uses: The coupling of the two key intermediates, N-(methoxycarbonyl)-l-tert-leucine acylated benzyl hydrazine and chloromethyl ketone, via an S N 2 reaction furnished the amino ketone in high yield under our optimized conditions in practical synthesis of the HIV Protease Inhibitor Atazanavir via a Highly diastereoselective Reduction Approach.

Technology Process of Methoxycarbonyl-L-tert-leucine

There total 3 articles about Methoxycarbonyl-L-tert-leucine 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: 100.0%

L-tert-Leucine (20859-02-3) + methyl chloroformate (79-22-1) → (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 60 ℃; for 18h; pH=8 - 9;

Reference yield: 74.0%

→ (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; water; at 20 ℃; for 5h; Cooling with ice;

Reference yield:

N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) → (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / toluene; water / 3 h / 60 °C

2: sodium hydroxide / water / 2 h / 25 °C / pH 10 - 13

With hydrogenchloride; sodium hydroxide; In water; toluene;

upstream raw materials:

L-tert-Leucine

methyl chloroformate

N-tert-butyloxycarbonyl-L-tert-leucine

Downstream raw materials:

methyl (1S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

((S)-1-{N'-[4-(2-tert-Butyl-2H-tetrazol-5-yl)-benzyl]-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyrylamino)-4-phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester

((S)-1-{(1S,2S)-1-Benzyl-3-[N-biphenyl-4-ylmethyl-N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-hydrazino]-2-hydroxy-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester

((S)-1-{N'-Biphenyl-4-ylmethyl-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester

Refernces

• 1、 Yeh, Teng-Kuang,Kang, Iou-Jiun,Hsu, Tsu-An,Lee, Yen-Chun,Lee, Chung-Chi,Hsu, Sheng-Ju,Tian, Ya-Wen,Yang, Hui-Yun,Chen, Chiung-Tong,Chao, Yu-Sheng,Yueh, Andrew,Chern, Jyh-Haur. "A novel, potent, and orally bioavailable thiazole HCV NS5A inhibitor for the treatment of hepatitis C virus". . p. 245 - 268. Retrieved 2019/02/19.
• 2、 You, Youngsu,Kim, Hee Sun,Bae, Il Hak,Lee, Seung Gi,Jee, Min Hyeok,Keum, Gyochang,Jang, Sung Key,Kim, B. Moon. "New potent biaryl sulfate-based hepatitis C virus inhibitors". . p. 87 - 100. Retrieved 2016/09/23.