C₂₈H₂₉NO₄

Base Information

• Chemical Name: C₂₈H₂₉NO₄
• CAS No.: 1446655-24-8
• Molecular Formula: C₂₈H₂₉NO₄
• Molecular Weight: 443.543
• Mol file: 1446655-24-8.mol

Synonyms:C₂₈H₂₉NO₄

Chemical Property of C₂₈H₂₉NO₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₈H₂₉NO₄

There total 10 articles about C₂₈H₂₉NO₄ 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: 72.0%

C21H23NO4 (1446655-22-6) + O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → C28H29NO4 (1446655-24-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 - 20 ℃; Inert atmosphere;

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → C28H29NO4 (1446655-24-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: thionyl chloride / Reflux

2.1: potassium carbonate / water; diethyl ether / 2 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 20 - 40 °C

4.1: cesium fluoride / N,N-dimethyl-formamide / 40 h / 60 °C

5.1: 1 h / 0 - 20 °C

5.2: 48 h / 20 °C

6.1: sodium hydroxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

6.2: pH 3 - 4

7.1: borane-THF / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

9.1: potassium hydrogencarbonate / 0.5 h / 0 °C

10.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -10 - 20 °C / Inert atmosphere

With thionyl chloride; borane-THF; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; potassium carbonate; potassium hydrogencarbonate; triethylamine; cesium fluoride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → C28H29NO4 (1446655-24-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / water; diethyl ether / 2 h / 0 - 20 °C

2.1: triethylamine / dichloromethane / 20 - 40 °C

3.1: cesium fluoride / N,N-dimethyl-formamide / 40 h / 60 °C

4.1: 1 h / 0 - 20 °C

4.2: 48 h / 20 °C

5.1: sodium hydroxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

5.2: pH 3 - 4

6.1: borane-THF / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

8.1: potassium hydrogencarbonate / 0.5 h / 0 °C

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -10 - 20 °C / Inert atmosphere

With borane-THF; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; potassium carbonate; potassium hydrogencarbonate; triethylamine; cesium fluoride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

C₂₁H₂₃NO₄

O-benzyl 2,2,2-trichloroacetimidate

4R-4-hydroxyproline

trans-4-hydroxy-L-proline ethyl ester hydrochloride

Downstream raw materials:

(2S,4S)-4-(benzyloxymethyl)-1-(2,2-diphenylacetyl)pyrrolidine-2-carboxylic acid

Refernces