Potassium Carbonate → (S)-(+)-2-Benzoyl-6-chloro-3-[(2-hydroxypropionyl)amino]indole

HRID 379758Notes

Reaction equation

HRID 379758 reaction equation
C([O:4][C@@H:5]([CH3:27])[C:6]([NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:19]([C:10]1[NH:11][C:12]2[C:17]([C:9]=1[NH:8][C:6](=[O:7])[C@@H:5]([OH:4])[CH3:27])=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 54496751(S)-(-)-3-(2-Acetoxypropionyl)amino-2-benzoyl-6-chloroindole

Product 1

HCID 53643334(S)-(+)-2-Benzoyl-6-chloro-3-[(2-hydroxypropionyl)amino]indoleYield 81.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (S)-(−)-3-(2-acetoxypropionylamino)-2-benzoyl-6-chloroindole (Example 58, 580 mg, 1.5 mmol) and potassium carbonate (2.0 g, 14 mmol) in ethanol (30 ml) and water (10 ml) was stirred for 2 h. The mixture was concentrated and extracted with ethyl acetate (50 ml×2). The organic extracts were dried (MgSO4) and concentrated to give a yellow amorphous solid. Recrystallization from ethyl acetate/hexane gave 420 mg (81%) of the title compound as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a yellow amorphous solid
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4ce3539c0044987a38bb5a7b410f745
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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