N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide

Base Information

• Chemical Name: N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide
• CAS No.: 1310344-46-7
• Molecular Formula: C₃₆H₅₀N₂O₃S
• Molecular Weight: 590.871
• Mol file: 1310344-46-7.mol

Synonyms:

Chemical Property of N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide

There total 6 articles about N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide 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: 83.0%

16α-hydroxy-4β,14α-dimethyl-20S-(methylamino)-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-11-one (1310344-32-1) + benzoic acid anhydride (93-97-0) → N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide (1310344-46-7)

Guidance literature:

In ethanol;

DOI:10.1016/j.ejmech.2011.02.073

Reference yield:

N-[(3β,4α,9β,16α,20S)-20-(dimethylamino)-16-hydroxy-4-(hydroxymethyl)-4,14-dimethyl-11-oxo-9,19-cyclopregnan-3-yl]-2-methylpropanamide → N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide (1310344-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / dichloromethane / 13 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine; toluene-4-sulfonic acid / 3.5 h / 20 - 90 °C / Inert atmosphere

3.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 5 h / 100 °C / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

3.3: 3 h / 10 °C / Inert atmosphere

4.1: water; potassium hydroxide / methanol / 5 h / 20 °C

5.1: trimethylaluminum / 1,2-dichloro-ethane; toluene / 3 h / Reflux; Inert atmosphere

6.1: ethanol

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; water; trimethylaluminum; toluene-4-sulfonic acid; potassium hydroxide; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1016/j.ejmech.2011.02.073

Reference yield:

20S-(dimethylamino)-3β-isobutyrylamino-4β,14α-dimethyl-4α-{[(p-methylbenzenesulfonyl)oxy]methyl}-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate (1310344-29-6) → N-{16α-hydroxy-4β,14α-dimethyl-11-oxo-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-20S-yl}-N-methylbenzamide (1310344-46-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 5 h / 100 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

1.3: 3 h / 10 °C / Inert atmosphere

2.1: water; potassium hydroxide / methanol / 5 h / 20 °C

3.1: trimethylaluminum / 1,2-dichloro-ethane; toluene / 3 h / Reflux; Inert atmosphere

4.1: ethanol

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; water; trimethylaluminum; potassium hydroxide; In methanol; ethanol; 1,2-dichloro-ethane; toluene;

DOI:10.1016/j.ejmech.2011.02.073

upstream raw materials:

16α-hydroxy-4β,14α-dimethyl-20S-(methylamino)-9,19-cyclo-{2'-isopropyl-5',6'-dihydro-4'αH-[1',3']thiazino[4',5':3,4]}-5α,9β-pregnan-11-one

benzoic acid anhydride

N-[20S-(dimethylamino)-3β-(isobutanamido)-4α-(hydroxymethyl)-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl] benzoate

20S-(dimethylamino)-3β-isobutyrylamino-4β,14α-dimethyl-4α-{[(p-methylbenzenesulfonyl)oxy]methyl}-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate