Ethyl Acetate → HCID 9947145, compound

HRID 382466Notes

Reaction equation

HRID 382466 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[C:23]([O:31][CH2:32][CH2:33][CH2:34][N:35]1[C:43]2[C:38](=[CH:39][C:40]([CH2:46][C@H:47]([NH2:49])[CH3:48])=[CH:41][C:42]=2[C:44]#[N:45])[CH2:37][CH2:36]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[C:23]([O:31][CH2:32][CH2:33][CH2:34][N:35]1[C:43]2[C:38](=[CH:39][C:40]([CH2:46][C@H:47]([NH2:49])[CH3:48])=[CH:41][C:42]=2[C:44]#[N:45])[CH2:37][CH2:36]1)(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 45108224(2R,3R)-2,3-Dihydroxybutanedioic acid--3-{5-[(2R)-2-aminopropyl]-7-cyano-2,3-dihydro-1H-indol-1-yl}propyl benzoate (1/1)

Product 1

HCID 9947145HCID 9947145, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of potassium carbonate (32.3 g) in distilled water(120 ml) was added ethyl acetate (120 ml), and (R)-3-[5-(2-aminopropyl)-7-cyano-2,3-dihydro-1H-indol-1-yl]propyl benzoate L-tartrate (12.0 g) was added portionwise to the mixture with stirring. After reaction for 1 hour, the reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with 10% aqueous potassium carbonate solution and brine subsequently, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give (R)-3-[5-(2-aminopropyl)-7-cyano-2,3-dihydro-1H-indol-1-yl]propyl benzoate (8.98 g) as a brown oil.

Workup

  1. additionwas added portionwise to the mixture
  2. customAfter reaction for 1 hour
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with 10% aqueous potassium carbonate solution and brine subsequently
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-88d2bfca419a4061a60d592948c85c44
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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