Trichloroacetic Acid → HCID 67296419, compound

HRID 2276854Notes

Reaction equation

HRID 2276854 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=2)=[CH:9][CH:8]=1)[CH3:2].C([C@@H]1N[C@H](C2OC(C)=CC=2)N(C)C1=O)C1C=CC=CC=1.ClC(Cl)(Cl)C(O)=O>C(OCC)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14]2)=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 11303220(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinoneHCID 67296304HCID 67296304, compound

Product 1

HCID 67296419HCID 67296419, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

{[4-(3-Oxo-1-cyclopenten-1-yl)phenyl]thio}acetic acid ethyl ester 378 mg (1.37 mmol) and (2S,5S)-5-benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone 54 mg (0.20 mmol) were dissolved in 10 mL of diethylether, followed by stirring at 0° C. Trichloroacetic acid 33 mg (0.20 mmol) and 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid t-butyl diester 340 mg (1.10 mmol) were added thereto, and the mixture was stirred for 12 days at room temperature. The solvent was concentrated, and purified by silica gel column chromatography (Biotage, solvent for elution; hexane/ethyl acetate) to give the title compound 187 mg (yield 67%).

Workup

  1. stirringthe mixture was stirred for 12 days at room temperature
  2. concentrationThe solvent was concentrated
  3. custompurified by silica gel column chromatography (Biotage, solvent for elution; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6265afdf020b40c2b133bea92d82f8af
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

Loading…