(alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide

Base Information

• Chemical Name: (alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide
• CAS No.: 1184940-47-3
• Molecular Formula: C18H18F2N2O4
• Molecular Weight: 364.349
• Mol file: 1184940-47-3.mol

Synonyms:EMD638683 (R-Form);Benzeneacetic acid, 3,5-difluoro-α-hydroxy-, 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide, (αR)-;(alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide

Chemical Property of (alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide

Chemical Property:

• Boiling Point: 657.6±55.0 °C(Predicted)
• PKA: 8.68±0.25(Predicted)
• PSA: 102.15000
• Density: 1.363
• LogP: 3.26700

Purity/Quality:

97% ^*data from raw suppliers

EMD638683R-Form 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide

There total 11 articles about (alphaR)-3,5-Difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide 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:

N'-[(R)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-4-benzyloxy-2-ethyl-3-methylbenzohydrazide (1184940-50-8) → N'-[(R)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide (1184940-47-3)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 30 ℃; under 760.051 Torr;

Reference yield:

EMD 638683 (1181770-72-8) → N'-[(R)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide (1184940-47-3) + N'-[(S)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide (1184940-46-2)

Guidance literature:

With Chiralpak AD column; In n-heptane; isopropyl alcohol; Resolution of racemate;

Reference yield:

N'-[2-(3,5-difluorophenyl)-2-oxoacetyl]-4-benzyloxy-2-ethyl-3-methylbenzohydrazide (1184940-49-5) → N'-[(R)-2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide (1184940-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 6.08 h / -78 - 20 °C

1.2: 20 °C

2.1: hydrogen / palladium 10% on activated carbon / methanol / 30 °C / 760.05 Torr

With dimethylsulfide borane complex; hydrogen; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; palladium 10% on activated carbon; In tetrahydrofuran; methanol; toluene;

upstream raw materials:

S-(+)-3.5-Difluoromandelic Acid

methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

2,3-dimethyl-4-methoxybenzaldehyde

4-methoxy-2,3-dimethyl-benzoic acid

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