Water → 2-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047890Notes

Reaction equation

HRID 1047890 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:28])=[C:18]([CH:24]=[C:25]([CH3:27])[CH3:26])[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593143192-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143752-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (764 mg, 2.02 mmol) is dissolved in EtOH (25 mL), and solid KOH (2.32 g, 40 mmol) and water (2.5 mL) are added. The mixture is stirred at RT for 30 min then concentrated in vacuo. The residue is dissolved in a mixture of water (40 mL) and EtOAc (20 mL) and the organic layer is separated. The aqueous layer is adjusted to approximately pH 7 with conc. HCl then extracted with EtOAc (2×15 mL). The combined organic layers are concentrated in vacuo to yield product (279) as off-white solid (544 mg, 78%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in a mixture of water (40 mL) and EtOAc (20 mL)
  3. customthe organic layer is separated
  4. extractionthen extracted with EtOAc (2×15 mL)
  5. concentrationThe combined organic layers are concentrated in vacuo

Sources & evidence

ORD record
ord-3be2367fa1b04c3f8e76d3bbf19bc8fc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…