HCID 178461288, compound → HCID 178461289, compound

HRID 1913542Notes

Reaction equation

HRID 1913542 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH:12]=[C:11](/[CH:13]=[C:14]3/[C:15](=[O:20])[NH:16][CH2:17][CH2:18][O:19]/3)[N:10]=[CH:9]2)[CH2:4][CH2:3]1>[C].[Pd].C(O)C>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH:12]=[C:11]([CH2:13][CH:14]3[O:19][CH2:18][CH2:17][NH:16][C:15]3=[O:20])[N:10]=[CH:9]2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 178461288HCID 178461288, compound

Product 1

HCID 178461289HCID 178461289, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

10% palladium-carbon catalyst (hydrated, 300 mg) was suspended in a solution of the compound (330 mg) obtained in Step 1 of this Example in ethanol (8 mL). The suspension was stirred under a hydrogen atmosphere at normal pressure at room temperature for 1 hour and at 45° C. for 1 hour. The reaction solution was filtered through celite, and the filtrate was concentrated. The obtained crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride/methanol=20/1-10/1) to obtain the title compound (325 mg).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (eluting solvent: methylene chloride/methanol=20/1-10/1)

Sources & evidence

ORD record
ord-65eeebc5415147b9af25c1b94b499fd4
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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