HCID 11242609, compound → HCID 18331717, compound

HRID 2270455Notes

Reaction equation

HRID 2270455 reaction equation
C(O[C:5]1[C:9](N=C=O)=[CH:8][S:7][C:6]=1/[C:13](=[CH:15]/[CH:16]([CH3:18])[CH3:17])/[CH3:14])(C)C.[CH:19]([O:22][C:23](NC1C=CSC=1/C(=C\C(C)C)/C)=[O:24])([CH3:21])[CH3:20].C(OC(NC1C=CSC=1C(CC(C)C)=C)=O)(C)C>[C].[Pd].CO>[CH:19]([O:22][C:23]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH:13]([CH3:14])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:24])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 11242609HCID 11242609, compoundHCID 11437086HCID 11437086, compoundHCID 86757678HCID 86757678, compound

Product 1

HCID 18331717HCID 18331717, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2.06 g (7.72 mmol) of the mixture of 3-isopropoxy-carbonylamino-{2-(E)-(4-methyl-2-penten-2-yl)}thiophene, 3-isopropoxycarbonylamino-{2-(Z)-(4-methyl-2-penten-2-yl)}thiophene, and 3-isopropoxycarbonylamino-{2-(4-methyl-1-penten-2-yl)}thiophene obtained in Example 13 and 0.41 g of 5% palladium carbon (Degussa chemical catalyst E106R/W) were charged into 20 ml of methanol, and after nitrogen purge, a hydrogenation reaction was conducted at normal pressure under hydrogen atmosphere for 9 hours. After nitrogen purge, the catalyst was filtrated off, and the solvent was distilled off under reduced pressure. The resulted residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 1.61 g of the intended compound as a colorless crystal (yield: 70%).

Workup

  1. customafter nitrogen purge
  2. customa hydrogenation reaction
  3. customAfter nitrogen purge
  4. filtrationthe catalyst was filtrated off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulted residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-886f055ead1f49e2b50e283936d26044
Source dataset
uspto-grants-2001_12
Patent number
US06331639B2

Reaction notes

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