Potassium Hydroxide → (R)-3-(2-Methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253653Notes

Reaction equation

HRID 1253653 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20]C)=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7]>C(O)C.O>[CH3:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[C:6]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59505253(R)-Methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 59505670(R)-3-(2-Methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (1 mol/laq) (2 eq.) was added to a suspension of (R)-methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-09) (0.61 mmol, 1 eq.) in a mixture of ethanol (3.6 ml) and water (0.8 ml). The reaction mixture was stirred at room temperature overnight. Ethanol was removed in vacuo and the aqueous residue was diluted with diethyl ether and dist. water. The phases were separated and the aqueous phase was acidified with 1N HCl to pH 3 and then extracted 4× with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated in vacuo to yield the desired product (E-09). Yield: 88%

Workup

  1. customEthanol was removed in vacuo
  2. additionthe aqueous residue was diluted with diethyl ether and dist
  3. customThe phases were separated
  4. extractionextracted 4× with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2f1c271dcc4bc695537e67ac02132f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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