Browse Prior Art Database

Synthesis of 6A,6B,6C,6D,6E,6F,6G,6H-octakis-S-(2-carboxyethyl)- 6A,6B,6C,6D,6E,6F,6G,6H -octathio-γ-Cyclodextrin Sodium salt

IP.com Disclosure Number: IPCOM000249262D
Publication Date: 2017-Feb-15
Document File: 2 page(s) / 219K

Publishing Venue

The IP.com Prior Art Database

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 63% of the total text.

Synthesis of 6 A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octakis-S-(2-carboxyethyl)-

6 A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octathio-γ-Cyclodextrin Sodium salt

6 A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octakis-S-(2-carboxyethyl)- 6

A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octathio-γ-

Cyclodextrin Sodium salt referred to as Compound I, has the following chemical structure:

Compound I

Provided herein is a process for preparing Compound I and intermediates thereof.

Step 1: Preparation of 6 A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octakis-S-(2-carboxyethyl)-6

A ,6

B ,6

C ,6

D ,6

E ,6

F ,

6 G

,6 H

-octathio-γ-Cyclodextrin Lithium salt (referred to as Compound II)

To a solution of 10g of 6-perdeoxy-6-perchloro-gamma-cyclodextrin (can be obtained by any

process described in the literature, for example Supramol. Chem., 2000, p 221) in DMF (200mL),

lithium hydroxide monohydrate and 3-mercaptopropionic acid were added at 25°C. The reaction

mixture was heated to 70°C and maintained at this temperature for 2-3 days. The reaction mixture

was cooled to 25°C, and then methanol (400mL) was added and stirred for 30 min at the same

temperature. The resultant solid was filtered, washed with methanol (40mL) and dried under

vacuum at 50°C in inert atmosphere to afford compound II as white solid.

Step 2: Preparation of 6 A ,6

B ,6

C ,6

D ,6

E ,6

F ,6

G ,6

H -octakis-S-(2-carboxyethyl)-6

A ,6

B ,6

C ,6

D ,6

E ,6

F ,

6 G

,6 H

-octathio-γ-Cyclodextrin Sodium salt (Compound I)

Compound II was dissolved in water (27mL) at room temperature. Acetone was added to the

s...