Ethyl Acetate → HCID 86753795, compound

HRID 1417602Notes

Reaction equation

HRID 1417602 reaction equation
C([O:8][C:9]1[C:10]2[CH2:23][C@:22]3([CH3:36])[C@@H:24]([CH3:35])[CH2:25][CH2:26][C@H:27]4[C:28]([CH3:34])([CH3:33])[C@@H:29]([OH:32])[CH2:30][CH2:31][C@@:21]34[O:20][C:11]=2[C:12]2[CH:13]([OH:19])[NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)C1C=CC=CC=1.C(OCC)(=O)C>C1COCC1.[C].[Pd]>[OH:19][CH:13]1[C:12]2[C:11]3[O:20][C@@:21]45[CH2:31][CH2:30][C@H:29]([OH:32])[C:28]([CH3:34])([CH3:33])[C@@H:27]4[CH2:26][CH2:25][C@H:24]([CH3:35])[C@@:22]5([CH3:36])[CH2:23][C:10]=3[C:9]([OH:8])=[CH:17][C:16]=2[C:15](=[O:18])[NH:14]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86753791HCID 86753791, compound

Product 1

HCID 86753795HCID 86753795, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the above Compound (29a) (100 mg, 0.20 mmol) dissolved in 5.0 ml of THF and 2.0 ml of ethyl acetate was added 45 mg of 10% palladium-carbon, and the mixture stirred at room temperature for 3 hours under hydrogen atmosphere. The palladium-carbon was filtered off, and the filtrate concentrated under reduced pressure. The residue was then purified by a silica gel column chromatography (silica gel 5.2 g; ethyl acetate) to give 78 mg (96%) of Compound (30a).

Workup

  1. filtrationThe palladium-carbon was filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was then purified by a silica gel column chromatography (silica gel 5.2 g; ethyl acetate)

Sources & evidence

ORD record
ord-a7b10b70e7f64628b7985f8d5c3cc2c1
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

Loading…