Tetrahydrofuran → HCID 70060999, compound

HRID 2230308Notes

Reaction equation

HRID 2230308 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH:7]([NH:23][C:24](=[O:42])[CH:25]([NH:30]C(C(N1CCCCCC1)=O)=O)[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O1[CH2:48][CH2:47][CH2:46][CH2:45]1>[Pd]>[C:1]([O:5][C:6](=[O:43])[CH:7]([NH:23][C:24](=[O:42])[CH:25]([NH:30][C:24]([N:23]1[CH2:45][CH2:46][CH2:47][CH2:48][CH2:6][CH2:7]1)=[O:42])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 70059500HCID 70059500, compound

Product 1

HCID 70060999HCID 70060999, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of the product from Example 1 (0.20 g, 0.35 mmol) in 16 mL of tetrahydrofuran was hydrogenated at 52 psi over 20% Pd/C for 48 hours. The reaction mixture was filtered through Celite using methanol and concentrated. The resulting foam was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate). The product was isolated as a foam and dried under vacuum to give the title compound (0.16 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe resulting foam was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate)
  4. customThe product was isolated as a foam
  5. customdried under vacuum

Sources & evidence

ORD record
ord-19d962f3985142d9b6b590bb8d3ce2bf
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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