17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride

Base Information

• Chemical Name: 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride
• CAS No.: 133991-62-5
• Molecular Formula: C₂₆H₃₄O₉
• Molecular Weight: 490.551
• Mol file: 133991-62-5.mol

Synonyms:

Chemical Property of 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride

Chemical Property:

• Melting Point: 200 - 205°C

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

21-Deschloromethyl-21-O-EthoxycarbonylLoteprednolEtabonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 11-O-Ethoxycarbonyl Loteprednol Etabonate 17-Carboxylic Acid is derived from Prednisolone (P703740), which is a synthetic corticosteroid; metabolically interconvertible with prednisone. Hydrocortisone EP Impurity A.

Technology Process of 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride

There total 2 articles about 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride 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: 96.0%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + chloroformic acid ethyl ester (541-41-3) → 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride (133991-62-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 10 ℃; for 0.5h; Large scale;

Reference yield:

prednisolon (50-24-8,8056-11-9) → 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride (133991-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate / methanol; water / 0.5 h / Heating; Large scale

2: triethylamine / dichloromethane / 0.5 h / 0 - 10 °C / Large scale

With sodium periodate; triethylamine; In methanol; dichloromethane; water;

upstream raw materials:

prednisolon

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 0^2,7. 0^11,15]heptadeca-3,6-diene-14-carboxylic acid

chloroformic acid ethyl ester

Refernces

• 1、 -. "Loteprednol preparation method and ophthalmic composition of loteprednol". . . Retrieved 2017/09/01.