acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester

Base Information

• Chemical Name: acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester
• CAS No.: 543741-50-0
• Molecular Formula: C₂₇H₂₇FO₆S
• Molecular Weight: 498.572
• Mol file: 543741-50-0.mol

Synonyms:acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester

Chemical Property of acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester

There total 6 articles about acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester 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: 84.0%

(10R,11R)-11-[(2R)-2,3-dihydroxypropyl]-8-fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl acetate (543741-49-7) + p-toluenesulfonyl chloride (98-59-9) → acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester (543741-50-0)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In toluene; at 20 ℃; for 24h;

Reference yield:

(10R,11R)-11-[(2R)-2,3-dihydroxypropyl]-8-fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl acetate (543741-49-7) + p-toluenesulfonyl chloride (98-59-9) → acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester (543741-50-0) + C34H33FO8S2 (543741-62-4)

Guidance literature:

(10R,11R)-11-[(2R)-2,3-dihydroxypropyl]-8-fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl acetate; With pyridine; In toluene; for 0.0833333h;

p-toluenesulfonyl chloride; In toluene; at 25 ℃; for 16h;

With hydrogenchloride; water; In toluene; pH=1 - 2; Product distribution / selectivity;

Reference yield:

(11Z)-11-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-8-fluoro-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one (887611-88-3) → acetic acid 8-fluoro-11-[2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl ester (543741-50-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen; triethylamine / palladium 10% on activated carbon / isopropyl alcohol / 6 h

1.2: 1 h / 40 °C

2.1: sodium tetrahydroborate / isopropyl alcohol / 1 h / 0 - 20 °C / pH 7 / Aqueous phosphate buffer

3.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 8 h / 20 °C

4.2: 0 °C

5.1: triethylamine / di(n-butyl)tin oxide / toluene / 24 h / 20 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; triethylamine; palladium 10% on activated carbon; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; toluene;

upstream raw materials:

(10R,11R)-11-[(2R)-2,3-dihydroxypropyl]-8-fluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl acetate

p-toluenesulfonyl chloride

(11Z)-11-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-8-fluoro-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one

(11R)-11-{[(4R)-2,2-dimethyl-1,3-dioxolane-4-yl]methyl}-8-fluoro-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one