4-[5-Amino-2-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidin-1-ylacetamido]-N-benzyl-2,2-difluoro-3-oxo-5-phenylpentanamide

Base Information

• Chemical Name: 4-[5-Amino-2-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidin-1-ylacetamido]-N-benzyl-2,2-difluoro-3-oxo-5-phenylpentanamide
• CAS No.: 243462-36-4
• Molecular Formula: C₃₀H₂₆ClF₂N₅O₄
• Molecular Weight: 594.017
• Mol file: 243462-36-4.mol

Synonyms:Y-40018

Chemical Property of 4-[5-Amino-2-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidin-1-ylacetamido]-N-benzyl-2,2-difluoro-3-oxo-5-phenylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[5-Amino-2-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidin-1-ylacetamido]-N-benzyl-2,2-difluoro-3-oxo-5-phenylpentanamide

There total 7 articles about 4-[5-Amino-2-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidin-1-ylacetamido]-N-benzyl-2,2-difluoro-3-oxo-5-phenylpentanamide 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:

2-[5-benzyloxycarbonylamino-2-(3-chlorophenyl)-1,6-dihydro-6-oxo-1-pyrimidinyl]-N-[1-benzyl-3-[N-(benzyl)carbamoyl]-3,3-difluoro-2-oxopropyl]acetamide (243462-52-4) → Y-40018 (243462-36-4)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; at 20 ℃; for 16h;

DOI:10.1021/jm000497n

Reference yield:

N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde (59830-60-3,63219-70-5,68474-26-0) → Y-40018 (243462-36-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / aq. K₂CO₃ / tetrahydrofuran; methanol / 20 °C

2: 3-hydroxybenzotriazole hydrate; 1-[3(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride / dimethylformamide / 20 °C

3: H₂; 1 N aq. HCl / 10percent Pd/C / methanol / 15 h / 20 °C

4: N-ethylmorpholine; 1-[3(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; 3-hydroxybenzotriazole hydrate / dimethylformamide / 16 h / 20 °C

5: Dess-Martin periodinate / dimethylformamide / 14 h / 20 °C

6: H₂ / 10percent Pd/C / methanol / 16 h / 20 °C

With N-ethylmorpholine;; hydrogenchloride; hydrogen; potassium carbonate; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 10percent Pd/C; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 5: Dess-Martin oxidation;

DOI:10.1021/jm000497n

Reference yield:

4-benzyl-4-benzyloxycarbonylamino-2,2-difluoro-3-hydroxybutanoic acid → Y-40018 (243462-36-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 3-hydroxybenzotriazole hydrate; 1-[3(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride / dimethylformamide / 20 °C

2: H₂; 1 N aq. HCl / 10percent Pd/C / methanol / 15 h / 20 °C

3: N-ethylmorpholine; 1-[3(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; 3-hydroxybenzotriazole hydrate / dimethylformamide / 16 h / 20 °C

4: Dess-Martin periodinate / dimethylformamide / 14 h / 20 °C

5: H₂ / 10percent Pd/C / methanol / 16 h / 20 °C

With N-ethylmorpholine;; hydrogenchloride; hydrogen; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 10percent Pd/C; In methanol; N,N-dimethyl-formamide; 4: Dess-Martin oxidation;

DOI:10.1021/jm000497n

upstream raw materials:

2-[5-benzyloxycarbonylamino-2-(3-chlorophenyl)-1,6-dihydro-6-oxo-1-pyrimidinyl]-N-[1-benzyl-3-[N-(benzyl)carbamoyl]-3,3-difluoro-2-oxopropyl]acetamide

N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde

4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-5-phenyl-N-benzylpentanamide

2-[5-benzyloxycarbonylamino-2-(3-chlorophenyl)-1,6-dihydro-6-oxo-1-pyrimidinyl]-N-[1-benzyl-3-[N-(benzyl)carbamoyl]-3,3-difluoro-2-hydroxypropyl]acetamide

Refernces

• 1、 Akahoshi,Ashimori,Sakashita,Yoshimura,Eda,Imada,Nakajima,Mitsutomi,Kuwahara,Ohtsuka,Fukaya,Miyazaki,Nakamura. "Synthesis, structure - Activity relationships, and pharmacokinetic profiles of nonpeptidic difluoromethylene ketones as novel inhibitors of human chymase". . p. 1297 - 1304. Retrieved 2007/10/03.