R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

Base Information

• Chemical Name: R-2-hydroxy-4-phenylbutyric acid L-menthyl ester
• CAS No.: 110143-66-3
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Mol file: 110143-66-3.mol

Synonyms:R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

Chemical Property of R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

There total 7 articles about R-2-hydroxy-4-phenylbutyric acid L-menthyl ester 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: 62.4%

2-oxo-4-phenylbutyric acid L-menthyl ester (117530-33-3) → R-2-hydroxy-4-phenylbutyric acid L-menthyl ester (110143-66-3)

Guidance literature:

With hydrogen; In ethanol; water; at 50 ℃; under 7500.75 Torr; Pressure; Reagent/catalyst; Solvent; Temperature; Autoclave;

Reference yield:

(-)-menthol (2216-51-5) → R-2-hydroxy-4-phenylbutyric acid L-menthyl ester (110143-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / p-toluenesulfonic acid*H₂O / benzene / 5 h / Heating

2: 29 percent / H₂ / 5percent Pd/C / propan-2-ol / 5 h / 50 °C / 2280 Torr

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In isopropyl alcohol; benzene;

DOI:10.1021/jm00394a009

Reference yield:

(E)-2-oxo-4-phenyl-3-butenoic acid (1914-59-6) → R-2-hydroxy-4-phenylbutyric acid L-menthyl ester (110143-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / p-toluenesulfonic acid*H₂O / benzene / 5 h / Heating

2: 29 percent / H₂ / 5percent Pd/C / propan-2-ol / 5 h / 50 °C / 2280 Torr

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In isopropyl alcohol; benzene;

DOI:10.1021/jm00394a009

upstream raw materials:

2-oxo-4-phenylbutyric acid L-menthyl ester

(-)-menthol

2-hydroxy-4-phenylbutanoic acid

(E)-2-oxo-4-phenyl-3-butenoic acid

Downstream raw materials:

(S)-2-((2R,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

(S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-3-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

(S)-2-((2R,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-3-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

t-butyl α-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(R)-phenylperhydro-1,4-thiazepin-4-yl}acetate

Refernces

• 1、 Flynn,Beight. "An efficient synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate: A useful intermediate in the synthesis of converting enzyme inhibitors". . p. 423 - 426,423-426. Retrieved 2007/10/02.