HCID 89806721, compound → HCID 89806719, compound

HRID 1474587Notes

Reaction equation

HRID 1474587 reaction equation
C([O:8][C:9](=[O:33])[CH2:10][C@@H:11]([C:20]([NH:22][CH:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26])=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[C:27]1([CH:23]([NH:22][C:20](=[O:21])[C@H:11]([CH2:10][C:9]([OH:33])=[O:8])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:24][CH2:25][CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 89806721HCID 89806721, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89806719HCID 89806719, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.50 g of Compound 1 obtained in Synthesis Example 1 was dissolved in 15 mL of ethyl acetate, and 0.656 g of 5% palladium carbon (50% moisture content) was added thereto. Then, the inside of the reaction system was substituted with hydrogen, and the reaction system was stirred at room temperature overnight and subjected to hydrogenolysis. The 5% palladium carbon was filtered off, and washed with 80 mL of ethyl acetate. Then, the organic layers were combined, distilled under reduced pressure to remove ethyl acetate, and then dried under vacuum, thereby to give 2.58 g of Compound 2.

Workup

  1. filtrationThe 5% palladium carbon was filtered off
  2. washwashed with 80 mL of ethyl acetate
  3. distillationdistilled under reduced pressure
  4. customto remove ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-542cd1b8d75e438d9fa7d3fd849bc071
Source dataset
uspto-grants-2015_04
Patent number
US09018323B2

Reaction notes

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