HCID 90411407, compound → HCID 90412965, compound

HRID 1521967Notes

Reaction equation

HRID 1521967 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14](S(C4C=CC=CC=4)(=O)=O)[C:15]([C:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 2

HCID 90411407HCID 90411407, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90412965HCID 90412965, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 87C (2.35 g, 4.17 mmol) in ethanol (40 mL) was added to 20% palladium hydroxide on carbon (wet, 2.35 g, 1.707 mmol) in a stainless steel pressure bottle and was stirred at 50° C. for several days at 50 psi hydrogen. The mixture was filtered through a nylon membrane and concentrated. The residue was dissolved in 30 mL 1,4-dioxane and treated with 2 mL 20% sodium hydroxide. The mixture was heated at 90° C. for 4 hours and was concentrated. The residue was treated with water and extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified using an ISCO Companion flash system on silica eluting with dichloromethane/ethyl acetate (5:5 to 4:6) to afford the title compound. MS (ESI+) m/z 425.9 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 30 mL 1,4-dioxane
  4. additiontreated with 2 mL 20% sodium hydroxide
  5. concentrationwas concentrated
  6. additionThe residue was treated with water
  7. extractionextracted with ethyl acetate (twice)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified

Sources & evidence

ORD record
ord-8c3ee37737474102a3ae5acceaccb66c
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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