17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid

Base Information

• Chemical Name: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid
• CAS No.: 124651-01-0
• Molecular Formula: C₂₄H₃₃NO₃
• Molecular Weight: 383.531
• Mol file: 124651-01-0.mol

Synonyms:17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid

Chemical Property of 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.18E-14mmHg at 25°C
• Boiling Point: 582°Cat760mmHg
• Flash Point: 305.8°C
• PSA: 69.89000
• Density: 1.13g/cm³
• LogP: 5.61210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid

There total 17 articles about 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid 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: 85.0%

methyl 7β-estra-1,3,5(10)triene-3-carboxylate (124651-20-3) → 17β-(N-tert-butylcarbamoyl)estra-1,3,5(10)-triene-3-carboxylic acid (124651-01-0)

Guidance literature:

With sodium hydroxide; In methanol; for 0.75h; Heating;

DOI:10.1021/jo00101a028

Reference yield:

Estrone (53-16-7) → 17β-(N-tert-butylcarbamoyl)estra-1,3,5(10)-triene-3-carboxylic acid (124651-01-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 3 h

2: 88 percent / ZnI₂ / CH₂Cl₂ / 1.) reflux, 25 min, 2.) 20 - 25 deg C, 2 h, 35 min

3: 74 percent / POCl₃, pyridine / 9.5 h / Heating

4: 92 percent / H₂ / 10percent Pd/C / CH₂Cl₂ / 3.5 h / 1344.6 Torr

5: 100 percent / NaOH / ethane-1,2-diol / 7.5 h / 155 - 160 °C

6: 1.) DMF, (COCl)2 / 1.) CH₂Cl₂, 10 deg C, 4 h, 2.) CH₂Cl₂, 1.0 h

7: 86.5 percent / Et₃N, (FSO₂)2O / CH₂Cl₂ / 1.5 h / -8 °C

8: 87.2 percent / Et₃N, dppp / Pd(OAc)2 / dimethylsulfoxide / 1.5 h / 75 °C / 362 Torr

9: 85 percent / aq. NaOH / methanol / 0.75 h / Heating

With pyridine; sodium hydroxide; fluorosulfonyl anhydride; oxalyl dichloride; 1,3-bis-(diphenylphosphino)propane; hydrogen; triethylamine; N,N-dimethyl-formamide; trichlorophosphate; palladium diacetate; palladium on activated charcoal; zinc(II) iodide; In methanol; dichloromethane; ethylene glycol; dimethyl sulfoxide;

DOI:10.1021/jo00101a028

Reference yield:

methyl 17-(N-tert-butylcarbamoyl)estra-1,3,5(10),16-tetraene-3-carboxylate (124651-19-0) → 17β-(N-tert-butylcarbamoyl)estra-1,3,5(10)-triene-3-carboxylic acid (124651-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / PtO₂ / ethyl acetate; ethanol / 3 h

2: K₂CO₃, H₂O / methanol / 18 h / Heating

With water; hydrogen; potassium carbonate; platinum(IV) oxide; In methanol; ethanol; ethyl acetate;

DOI:10.1021/jm00165a009

upstream raw materials:

methyl 7β-estra-1,3,5(10)triene-3-carboxylate

17β-cyanoestra-1,3,5(10)-trien-3-ol

(8S,9S,13S,14S,17S)-3-Hydroxymethyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-carbaldehyde

Methyl 17β-cyano-estra-1,3,5(10)triene-3-carboxylate

Refernces

• 1、 Yamashita, Dennis S.,Holt, Dennis A.,Oh, Hye-Ja,Shah, Dinu,Yen, Hwa-Kwo,Brandt, Martin,Levy, Mark A.. "3-Carboxy-20-keto steroids are dual uncompetitive inhibitors of human steroid 5α-reductase types 1 and 2". . p. 1481 - 1485. Retrieved 2007/10/03.