Acetic Acid → HCID 58997665, compound

HRID 1592355Notes

Reaction equation

HRID 1592355 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]([CH3:26])[C@@H:10]([OH:25])[CH2:11][N:12]([CH2:23][CH3:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)C1C=CC=CC=1.CC(O)=O.CCOCC>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]([CH3:26])[C@@H:10]([OH:25])[CH2:11][N:12]([CH2:23][CH3:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 58997648HCID 58997648, compound

Product 1

HCID 58997665HCID 58997665, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

Pd(OH)2 was carefully wetted down under N2 with 5 mL of MeOH then the product of Step f (0.95 g) dissolved in 5 mL of MeOH was added followed by 5 mL of HOAc. The mixture was hydrogenated overnight on a Parr shaker at 50 psi. Worked up by filtering off the catalyst under N2 through a fiberglass filter paper and vacuum. The filtrate was stripped to obtain white glass. To white glass was added Et2O/saturated NaHCO3 (25 mL) The layers were separated. The aqueous was basified further with 1N NaOH to pH=12 and extracted 3 times with Et2O. The Et2O extracts from the 1N NaOH layer were combined, dried (Na2SO4) and stripped to give 0.40 g of and amber oil as product. MS (ESI) detects (M+H)+=269.

Workup

  1. additionwas added
  2. filtrationby filtering off the catalyst under N2 through a fiberglass
  3. filtrationfilter paper and vacuum
  4. customto obtain white glass
  5. customwere separated
  6. extractionextracted 3 times with Et2O
  7. dry with materialdried (Na2SO4)
  8. customto give 0.40 g of and amber oil as product

Sources & evidence

ORD record
ord-1411dd38f67542fb9b8f9194f23935e8
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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