17-TRIFLUOROMETHYLPHENYL TRINOR PROSTAGLANDIN F2ALPHA

Base Information

• Chemical Name: 17-TRIFLUOROMETHYLPHENYL TRINOR PROSTAGLANDIN F2ALPHA
• CAS No.: 221246-34-0
• Molecular Formula: C₂₄H₃₁F₃O₅
• Molecular Weight: 456.502
• Mol file: 221246-34-0.mol

Synonyms:5-Heptenoicacid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-[3-(trifluoromethyl)phenyl]-1-pentenyl]cyclopentyl]-,(5Z)- (9CI)

Chemical Property of 17-TRIFLUOROMETHYLPHENYL TRINOR PROSTAGLANDIN F2ALPHA

Chemical Property:

• Boiling Point: 593.0±50.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 97.99000
• Density: 1.296±0.06 g/cm3(Predicted)
• LogP: 4.11420

Purity/Quality:

99% ^*data from raw suppliers

17-trifluoromethylphenyl trinor Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A number of 17-phenyl trinor prostaglandin F2α (17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma. Of these, the unsubstituted or meta-substituted aromatic derivatives are the most potent FP receptor agonists. 17-trifluoromethylphenyl trinor PGF2α bears an aromatic ring which is reminiscent of the trifluoromethyl-phenoxy ring of travoprost ((+)-fluprostenol isopropyl ester). As an ocular hypotensive agent, it would be expected that 17-trifluoromethylphenyl trinor PGF2α would act very much like the free acid of travoprost. 17-phenyl trinor PGF2α is a potent luteolytic and abortifacient, with a potency equal to or greater than fluprostenol and cloprostenol.

Technology Process of 17-TRIFLUOROMETHYLPHENYL TRINOR PROSTAGLANDIN F2ALPHA

There total 10 articles about 17-TRIFLUOROMETHYLPHENYL TRINOR PROSTAGLANDIN F2ALPHA 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:

3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4) → 17-(3-trifluoromethylphenyl)-17-trinor prostaglandin F2α (221246-34-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: H₂ / 5 percent Pd/C / ethyl acetate

2.1: MeOH

3.1: N-BuLi / tetrahydrofuran / 0 °C

3.2: 80 percent / tetrahydrofuran

4.1: NaHMDS / 1,2-dimethoxy-ethane

4.2: 50 percent / 1,2-dimethoxy-ethane

5.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

6.1: K₂CO₃; MeOH

7.1: p-TSA / CH₂Cl₂

8.1: DIBAL-H / -78 °C

9.1: NaHMDS

10.1: aq. AcOH / tetrahydrofuran

With methanol; lithium aluminium tetrahydride; n-butyllithium; (-)-(S)-BINAL-H; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; 1.1: Catalytic hydrogenation / 2.1: Esterification / 3.1: Metallation / 3.2: Condensation / 4.1: Metallation / 4.2: Condensation / 5.1: Reduction / 6.1: deprotection / 7.1: Etherification / 8.1: reductive ring cleavage / 9.1: Metallation / 9.2: Condensation / 10.1: Hydrolysis;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-cyclopentyl}-hept-5-enoic acid (294856-07-8) → 17-(3-trifluoromethylphenyl)-17-trinor prostaglandin F2α (221246-34-0)

Guidance literature:

With acetic acid; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate (70783-99-2) → 17-(3-trifluoromethylphenyl)-17-trinor prostaglandin F2α (221246-34-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaHMDS / 1,2-dimethoxy-ethane

1.2: 50 percent / 1,2-dimethoxy-ethane

2.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

3.1: K₂CO₃; MeOH

4.1: p-TSA / CH₂Cl₂

5.1: DIBAL-H / -78 °C

6.1: NaHMDS

7.1: aq. AcOH / tetrahydrofuran

With methanol; lithium aluminium tetrahydride; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: deprotection / 4.1: Etherification / 5.1: reductive ring cleavage / 6.1: Metallation / 6.2: Condensation / 7.1: Hydrolysis;

DOI:10.1016/S0960-894X(00)00273-0

upstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-cyclopentyl}-hept-5-enoic acid

3-(trifluoromethyl)cinnamic acid

dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

3-(3-trifluoromethylphenyl)propanoic acid