HCID 86751788, compound → HCID 70271251, compound

HRID 1941449Notes

Reaction equation

HRID 1941449 reaction equation
[C:1]([O:5][C:6]([N:8]([C@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][C:24]([O:26]CC2C=CC=CC=2)=[O:25])[C:18]1=[O:34])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([C@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][C:24]([OH:26])=[O:25])[C:18]1=[O:34])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86751788HCID 86751788, compound

Product 1

HCID 70271251HCID 70271251, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 43 (1.06 g, 2.27 mol) in 35 mL of methanol was added 10% Pd/C catalyst (127 mg) and the mixture was hydrogenated on a Parr shaker apparatus at 45 PSI for 2 hrs. The solution was filtered, evaporated, and the residue was dried by pumping at <1 mm Hg vacuum for 10 hrs to afford 0.836 g (98% yield) of product 44 as a colorless foam. TLC (silica; CH2Cl2, methanol, acetic acid: 27, 3, 1) Rf=0.40.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customthe residue was dried
  4. waitby pumping at <1 mm Hg vacuum for 10 hrs

Sources & evidence

ORD record
ord-13e1c55242bc430d83e43cdfbfbc0e4e
Source dataset
uspto-grants-1997_12
Patent number
US05703208

Reaction notes

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