HCID 131720323, compound → HCID 131720322, compound

HRID 2293957Notes

Reaction equation

HRID 2293957 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][C:38]([O:40][CH3:41])=[O:39])[CH:12]=[CH:13][C:14]=1[C@H:15]1[C@H:18]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:28])[N:16]1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)C1C=CC=CC=1>CCOC(C)=O.CO>[OH:8][C:9]1[CH:10]=[C:11]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:12]=[CH:13][C:14]=1[C@H:15]1[C@H:18]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:28])[N:16]1[C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 131720323HCID 131720323, compound

Product 1

HCID 131720322HCID 131720322, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve the product of Example 5 (0.266 g, 0.48 mmol) in EtOAc (16 mL), dilute with CH3OH (20 mL) and purge with N2. Add 20% Pd/C (0.05 g), purge the mixture with H2 and then stir under a balloon of H2 overnight. Filter the reaction mixture through celite. Wash the filter cake with EtOAc and concentrate the filtrate to give 0.156 g of the title compound as a colorless oil. HRMS calc'd for C28H28 NO4 :M+H 462.2081; found 462.2070.MS (CI): 462 (M+1,37), 351 (17), 293(41 ), 138(100).

Workup

  1. custompurge with N2
  2. additionAdd 20% Pd/C (0.05 g)
  3. custompurge the mixture with H2
  4. filtrationFilter the reaction mixture through celite
  5. washWash the filter cake with EtOAc
  6. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-89a1988a52f64db58c76f0a4fe67bc06
Source dataset
uspto-grants-1997_11
Patent number
US05688785

Reaction notes

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