HCID 69837885, compound → HCID 44402878, compound

HRID 352370Notes

Reaction equation

HRID 352370 reaction equation
C([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][N:21]3[C:24]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=4)=[CH:28][CH:27]=3)=[O:25])=[CH:17][C:16]=2[O:43][CH3:44])[CH2:10][C@H:9]1[CH3:45])C1C=CC=CC=1>CCO.C1COCC1.[Pd]>[CH3:45][C@H:9]1[NH:8][C@@H:13]([CH3:14])[CH2:12][N:11]([C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][N:21]3[C:24]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=4)=[CH:28][CH:27]=3)=[O:25])=[CH:17][C:16]=2[O:43][CH3:44])[CH2:10]1

Participants

5

Reactant 1

HCID 69837885HCID 69837885, compound

Product 1

HCID 44402878HCID 44402878, compoundYield 98.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of D6 (380 mg, 0.64 mmole) in EtOH (50 ml) and THF (50 ml) was treated with 10% Pd-C (300 mg) and stirred under a hydrogen atmosphere at ambient temperature and pressure for 70 h. The mixture was filtered through Kieselguhr and concentrated under vacuum. The residue was purified by chromatography on basic alumina eluting with EtOAc followed by crystallisation from Et2O to afford the title compound as a yellow solid (320 mg, 98%). MH+507.

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by chromatography on basic alumina eluting with EtOAc
  4. customfollowed by crystallisation from Et2O

Sources & evidence

ORD record
ord-1960e1a222d04d91898fc1d3a4aea385
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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