Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester
• CAS No.: 116940-94-4
• Molecular Formula: C₁₈H₁₉ClN₂O₃
• Molecular Weight: 346.813
• Mol file: 116940-94-4.mol

Synonyms:

Chemical Property of Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

There total 11 articles about Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester 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:

(+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione benzoate (116891-16-8) → Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester (116940-94-4)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In chloroform; for 6h; Heating;

DOI:10.1139/v88-009

Reference yield:

cis-1,3-cyclopentanedicarboxylic acid anhydride (6054-16-6) → Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester (116940-94-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) r.t., 19 h; 2.) 2 deg C, 12 days

2: 26.2 g / thionyl chloride, pyridine, DMF / benzene / 2 h / Heating

3: 16.01 g / NH₃ / benzene / 0.5 h

4: 85.7 percent / lithium borohydride / tetrahydrofuran / 2 h / Heating

5: 74 percent / Ba(OH)2*8H₂O, bromine / H₂O / 1.) r.t., 2 h; 2.) 50-65 deg C, 1.25 h

6: 71 percent / dimethylformamide; benzene / Ambient temperature

7: 82 percent / 2N H₂SO₄ / 1.08 h / 100 °C

8: 0.822 g / pyridine / 48 h / 55 °C

9: 0.429 g / 1M hydrochloric acid / ethanol; H₂O / 24 h / Heating

10: thionyl chloride, DMF / CHCl₃ / 6 h / Heating

With pyridine; hydrogenchloride; barium dihydroxide; lithium borohydride; thionyl chloride; sulfuric acid; ammonia; bromine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; chloroform; water; N,N-dimethyl-formamide; benzene;

DOI:10.1139/v88-009

Reference yield:

cis-1,3-cyclopentanedicarboxylic acid (876-05-1,826-02-8) → Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester (116940-94-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 79 percent / acetic anhydride / 0.5 h / Heating

2: 1.) r.t., 19 h; 2.) 2 deg C, 12 days

3: 26.2 g / thionyl chloride, pyridine, DMF / benzene / 2 h / Heating

4: 16.01 g / NH₃ / benzene / 0.5 h

5: 85.7 percent / lithium borohydride / tetrahydrofuran / 2 h / Heating

6: 74 percent / Ba(OH)2*8H₂O, bromine / H₂O / 1.) r.t., 2 h; 2.) 50-65 deg C, 1.25 h

7: 71 percent / dimethylformamide; benzene / Ambient temperature

8: 82 percent / 2N H₂SO₄ / 1.08 h / 100 °C

9: 0.822 g / pyridine / 48 h / 55 °C

10: 0.429 g / 1M hydrochloric acid / ethanol; H₂O / 24 h / Heating

11: thionyl chloride, DMF / CHCl₃ / 6 h / Heating

With pyridine; hydrogenchloride; barium dihydroxide; lithium borohydride; thionyl chloride; sulfuric acid; ammonia; bromine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; chloroform; water; acetic anhydride; N,N-dimethyl-formamide; benzene;

DOI:10.1139/v88-009

upstream raw materials:

(+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione benzoate

cis-1,3-cyclopentanedicarboxylic acid anhydride

cis-1,3-cyclopentanedicarboxylic acid

(+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate

Refernces