HCID 66602596, compound → HCID 66602584, compound

HRID 2097535Notes

Reaction equation

HRID 2097535 reaction equation
C([O:8][CH2:9][C:10]1[NH:11][C:12]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:21]=2)=[CH:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH:29]1([O:28][C:22]2[CH:21]=[C:20]([C:12]3[NH:11][C:10]([CH2:9][OH:8])=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=3)[CH:25]=[CH:24][C:23]=2[O:26][CH3:27])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 2

HCID 66602596HCID 66602596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66602584HCID 66602584, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To 280 ml of ethanol solution containing 3.15 g (7.0 mmol) of ethyl 2-benzyloxymethyl-5-(3-cyclopentoxy-4-methoxyphenyl)-1H-pyrrol-3-carboxylate obtained in Reference example 47-(c) was added 600 mg of 10% palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 11 hours. Then, the mixture was stirred at 30° C. for 1.25 hours, and further at 40° C. for 13 hours. After completion of the reaction, the reaction suspension was filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3→1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.09 g of the title compound as a yellowish oil. (Yield: 43%)

Workup

  1. waitfurther at 40° C. for 13 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction suspension was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionthe fractions containing the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc8ad32172f0465cbae5a73fede01f5e
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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