Ethyl Acetate → HCID 69001877, compound

HRID 1909772Notes

Reaction equation

HRID 1909772 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21](O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CCOC(C)=O>CO.CC(O)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 68999301HCID 68999301, compound

Product 1

HCID 69001877HCID 69001877, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To product from step 2 (50 mg, 0.13 mM) was added Pd/C 10% (40 mg, wt) in MeOH/AcOH (1.5 ml, 6:4) and stirred under H2 (H2 balloon, atm pr) for 6 h. 10% NaOH (5 mL) was added to quench the reaction. EtOAc was added and the mixture was filtered and dried down to give the title compound (29 mg, 83%).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationthe mixture was filtered
  4. customdried down

Sources & evidence

ORD record
ord-de6711658d7848e5ada336e6d1c92723
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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