(2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid

Base Information

• Chemical Name: (2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid
• CAS No.: 96561-53-4
• Molecular Formula: C17H13NO7
• Molecular Weight: 343.293
• Mol file: 96561-53-4.mol

Synonyms:(2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid

Chemical Property of (2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid

Chemical Property:

• Boiling Point: 661.6±55.0 °C(Predicted)
• PKA: 3.20±0.11(Predicted)
• PSA: 135.37000
• Density: 1.673±0.06 g/cm3(Predicted)
• LogP: 0.81850

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: L-Threo-(n-phthaloyl-3-(3,4-dihydroxyphenyl)serine) is a useful intermediate for the preparation of Droxidopa; a prodrug for the treatment of hypotension.

Technology Process of (2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid

There total 4 articles about (2S,3R)-3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propionic acid 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:

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanoic acid (96561-34-1,96614-52-7) → L-threo-(N-phthaloyl-3-(3,4-dihydroxyphenyl)serine) (96561-53-4)

Guidance literature:

With aluminum (III) chloride; Octanethiol; In dichloromethane; at -20 - 15 ℃; Large scale;

Reference yield:

phthalimide (136918-14-4,85-41-6) → L-threo-(N-phthaloyl-3-(3,4-dihydroxyphenyl)serine) (96561-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / N,N-dimethyl-formamide / 2 h / -10 - 30 °C / Large scale

2.1: sodium carbonate / water / 15 - 35 °C / Large scale

2.2: 2.5 h / 15 - 25 °C / pH 1 - 2 / Large scale

3.1: methanol / 3 h / 25 - 30 °C / Large scale

4.1: sulfuric acid / water / 6 h / 15 - 50 °C / pH < 2 / Large scale

5.1: aluminum (III) chloride; Octanethiol / dichloromethane / -20 - 15 °C / Large scale

With aluminum (III) chloride; Octanethiol; sulfuric acid; sodium carbonate; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

N-methoxycarbonylphthalimide (25543-10-6) → L-threo-(N-phthaloyl-3-(3,4-dihydroxyphenyl)serine) (96561-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium carbonate / water / 15 - 35 °C / Large scale

1.2: 2.5 h / 15 - 25 °C / pH 1 - 2 / Large scale

2.1: methanol / 3 h / 25 - 30 °C / Large scale

3.1: sulfuric acid / water / 6 h / 15 - 50 °C / pH < 2 / Large scale

4.1: aluminum (III) chloride; Octanethiol / dichloromethane / -20 - 15 °C / Large scale

With aluminum (III) chloride; Octanethiol; sulfuric acid; sodium carbonate; In methanol; dichloromethane; water;

upstream raw materials:

phthalimide

N-methoxycarbonylphthalimide

2-phthalimido-3-hydroxy-3-(3,4-methylenedioxyphenyl)propionic acid

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanoic acid