(alphaS)-3,5-difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide

Base Information

• Chemical Name: (alphaS)-3,5-difluoro-alpha-hydroxybenzeneacetic acid 2-(2-ethyl-4-hydroxy-3-methylbenzoyl)hydrazide
• CAS No.: 1184940-46-2
• Molecular Formula: C18H18F2N2O4
• Molecular Weight: 364.34
• Mol file: 1184940-46-2.mol

Synonyms:EMD 638683 (S-Form);EMD-638683 (S-Form);

Chemical Property of (alphaS)-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:

98% ^*data from raw suppliers

EMD638683S-Form 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 9 articles about (alphaS)-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:

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:

S-(+)-3.5-Difluoromandelic Acid (132741-31-2) → 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:

Multi-step reaction with 5 steps

1: boric acid / methanol / 18 h / 20 °C

2: hydrazine hydrate / isopropyl alcohol / 18 h / Reflux

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

4: boron tribromide / dichloromethane / 3 h / 20 °C

5: Chiralpak AD column / isopropyl alcohol; n-heptane / Resolution of racemate

With boric acid; boron tribromide; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate (208259-37-4,209982-92-3) → 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:

Multi-step reaction with 4 steps

1: hydrazine hydrate / isopropyl alcohol / 18 h / Reflux

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

3: boron tribromide / dichloromethane / 3 h / 20 °C

4: Chiralpak AD column / isopropyl alcohol; n-heptane / Resolution of racemate

With boron tribromide; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In n-heptane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

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

Refernces