Deflazacort

Base Information

• Chemical Name: Deflazacort
• CAS No.: 13649-88-2
• Molecular Formula: C23H29NO4
• Molecular Weight: 383.488
• Hs Code.: 2937290090
• Mol file: 13649-88-2.mol

Synonyms:5'H-Pregna-1,4-dieno[17,16-d]oxazole-3,20-dione,11-hydroxy-2'-methyl-, (11b,16b)-;

Chemical Property of Deflazacort

Chemical Property:

• Vapor Pressure: 4.13E-14mmHg at 25°C
• Melting Point: >250°C (dec.)
• Refractive Index: 1.675
• Boiling Point: 544.2 °C at 760 mmHg
• PKA: 14.35±0.70(Predicted)
• Flash Point: 282.9 °C
• PSA: 75.96000
• Density: 1.39 g/cm³
• LogP: 2.45560
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99.00% ^*data from raw suppliers

21-DeacetoxyDeflazacort ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate of Deflazacort (D228975), a systematic corticosteroid.

Technology Process of Deflazacort

There total 9 articles about Deflazacort 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:

3β,11β-dihydroxy-2'-methyl-(5α,16β)-pregnano[17,16-d]oxazol-20-one (13649-86-0) → 11β-hydroxy-2'-methyl-(16β)-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (13649-88-2)

Guidance literature:

Multi-step reaction with 6 steps

1: Py

2: MeSO₂Cl, SO₂, collidine / dimethylformamide

3: aq. KOH / methanol / Heating

4: aq. CrO₃ / acetone

5: (i) Br₂, aq. HBr, AcOH, dioxane, (ii) LiBr, Li₂CO₃, DMF

6: (i) AcNHBr, HClO₄, THF, (ii) Cr(OAc)2, nBuSH, DMSO

With pyridine; chromium(VI) oxide; 2,3,5-trimethyl-pyridine; potassium hydroxide; sulfur dioxide; methanesulfonyl chloride; In methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0039-128X(69)90046-4

Reference yield:

3β,11β-dihydroxy-2'-methyl-(5α,16β)-pregnano[17,16-d]oxazol-20-one semicarbazone (13649-85-9) → 11β-hydroxy-2'-methyl-(16β)-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (13649-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl / methanol / 1 h / Heating

2: Al(OiPr)3 / toluene; cyclohexanone / 2 h / Heating

3: (i) Br₂, HBr, AcOH, dioxane, (ii) LiBr, Li₂CO₃, DMF

With hydrogenchloride; aluminum isopropoxide; In methanol; cyclohexanone; toluene;

DOI:10.1021/jm00317a009

Reference yield:

3β-hydroxy-2'-methyl-(5α,16β)-pregnano[17,16-d]oxazole-11,20-dione 20-semicarbazone (16119-50-9) → 11β-hydroxy-2'-methyl-(16β)-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (13649-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1: (i) KHCO₃, aq. EtOH, (ii) aq. NaBH₄

2: aq. HCl / methanol / 1 h / Heating

3: Al(OiPr)3 / toluene; cyclohexanone / 2 h / Heating

4: (i) Br₂, HBr, AcOH, dioxane, (ii) LiBr, Li₂CO₃, DMF

With hydrogenchloride; aluminum isopropoxide; In methanol; cyclohexanone; toluene;

DOI:10.1021/jm00317a009

upstream raw materials:

11β-hydroxy-2'-methyl-(5α,16β)-pregnano[17,16-d]oxazole-3,20-dione

2'-methyl-(16β)-pregna-1,4,9(11)-trieno[17,16-d]oxazole-3,20-dione

3β-hydroxy-2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazol-20-one

2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazole-3,20-dione

Downstream raw materials:

deflazacort

21-acetoxy-2'-methyl-(16β)-pregna-1,4,9(11)-trieno[17,16-d]oxazole-3,20-dione

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