ent-Aprepitant

Base Information

• Chemical Name: ent-Aprepitant
• CAS No.: 172822-29-6
• Molecular Formula: C23H21F7N4O3
• Molecular Weight: 534.4266624
• Hs Code.: 2934990002
• Mol file: 172822-29-6.mol

Synonyms:ent-Aprepitant;Aprepitant Related Compound B (10 mg) (3-[[(2S,3R)-2-[(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholino]methyl]-1H-1,2,4-triazol-5(4H)-one);[2S-[2α(R*),3α]]-5-[[2-[1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-Morpholinyl]Me;5-[[(2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-Morpholinyl]Methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one;Aprepitant Related CoMpound B;Aprepitant EP Impurity D;Aprepitant B

Chemical Property of ent-Aprepitant

Chemical Property:

• PKA: 8.06±0.20(Predicted)
• PSA: 83.50000
• Density: 1.51±0.1 g/cm3(Predicted)
• LogP: 5.30230

Purity/Quality:

98% ^*data from raw suppliers

ent-Aprepitant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The (S,R,S)-enantiomer of Aprepitant (A729800), an unwanted enantiomer of Aprepitant in bulk drug and formulation samples of Aprepitant. ent-Aprepitant (Aprepitant EP Impurity D) is the (S,R,S)-enantiomer of Aprepitant (A729800), an unwanted enantiomer of Aprepitant in bulk drug and formulation samples of Aprepitant.

Technology Process of ent-Aprepitant

There total 9 articles about ent-Aprepitant 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: 98.0%

(2S,3R)-2-[(1S)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine (327623-37-0) + 3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one (252742-72-6) → 5-[{(2S,3R)-2-((1S)-1-3,5-bis(trifluoro-methyl)phenylethoxy)-3-(4-fluorophenyl)-4-morpholinyl}methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one (172822-29-6,221350-96-5)

Guidance literature:

With potassium carbonate; In water; N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1080/00397910903221084

Reference yield:

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5) + N'-(1-amino-2-chloroethylidene)hydrazine carboxylic acid methyl ester → 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one (172822-29-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 120 ℃; for 3h;

Reference yield:

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one (252742-72-6) + [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5) → 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one (172822-29-6)

Guidance literature:

With potassium carbonate; In water; N,N-dimethyl-formamide; at 0 ℃; for 4h;

upstream raw materials:

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one

2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]-1-iminoethyl]hydrazinecarboxylic acid methyl ester

(2S,3R)-2-[(1S)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine

Refernces

• 1、 Gangula, Srinivas,Elati, Chandrashekhar R.,Mudunuru, Satish Varma,Nardela, Anitha,Dongamanti, Ashok,Bhattacharya, Apurba,Bandichhor, Rakeshwar. "Synthesis of all enantiomerically pure diastereomers of aprepitant". experimental part. p. 2254 - 2268. Retrieved 2010/09/11.