Triethylamine → HCID 14013805, compound

HRID 1763130Notes

Reaction equation

HRID 1763130 reaction equation
Cl[C:2]([F:28])([F:27])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:4]=1[C:23]([O:25][CH3:26])=[O:24].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[CH2:21]([N:18]([CH2:19][CH3:20])[C:5]1[C:4]([C:23]([O:25][CH3:26])=[O:24])=[C:3]([CH:2]([F:27])[F:28])[N:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14013804HCID 14013804, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14013805HCID 14013805, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.5 g (0.006 mol) of product of Example 53, 0.61 g (0.006 mol) of triethylamine and 0.12 g of Pd/C (10%) in 35 ml of ethanol was hydrogenated at 50° C. under 480 kPa of hydrogen pressure for 45 minutes. Reaction mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in ether, washed with 10% HCl and the aqueous 10% HCl layer was extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated in vacuo to 1.91 g. Crude was kugelrohr distilled at 109 Pa, pot temperature 99° C., affording 1.63 g (68.2%) of this product as a yellow oil, nD25 1.4682.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with 10% HCl
  6. extractionthe aqueous 10% HCl layer was extracted with chloroform
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated in vacuo to 1.91 g
  9. distillationCrude was kugelrohr distilled at 109 Pa, pot temperature 99° C.

Sources & evidence

ORD record
ord-4af0277a86c0450f9aa2ef57ed930a8b
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

Loading…