Water → HCID 11429891, compound

HRID 734746Notes

Reaction equation

HRID 734746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[F:28])[NH:24][N:23]=[CH:22]3)=[O:17])=[CH:4][C:3]=1[N+:29]([O-])=O.Cl[Sn]Cl.O.[OH-].[Na+]>CCOC(C)=O>[NH2:29][C:3]1[CH:4]=[C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[F:28])[NH:24][N:23]=[CH:22]3)=[O:17])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 57845275HCID 57845275, compound

Product 1

HCID 11429891HCID 11429891, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product (222 mg, 0.5 mmol, 1.0 equiv.) from Example 76, Step 3 was dissolved in EtOAc (50 mL) and SnCl2 (380 mg, 2.0 mmol, 4 equiv.) and H2O (0.5 mL) were added. The mixture was refluxed for 3 h. After the reaction was cooled to room temperature, 2N NaOH was added and the mixture was stirred for 30 min. The biphasic solution was filtered through the Celite, and the phases were separated. The organic phase was washed twice with brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give the title compound in 64% yield. MS (ES+) m/e 414 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe biphasic solution was filtered through the Celite
  3. customthe phases were separated
  4. washThe organic phase was washed twice with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-98a5d7ca5bb24a11b0ad22689872135d
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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