Water → 2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047897Notes

Reaction equation

HRID 1047897 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[C:19]([CH3:25])[C:18]=2[O:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[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>C(O)C>[CH:27]1([O:26][C:18]2[C:19]([CH3:25])=[CH:20][C:21]([CH2:23][OH:24])=[CH:22][C:17]=2[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:31])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593141022-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593142062-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (70 mg, 0.16 mmol) is dissolved in ethanol (1.5 mL), and solid KOH (191 mg, 3.3 mmol) and water (1504) are added. The mixture is stirred at room temperature for 30 min then concentrated in vacuo. The residue is dissolved in water (1.5 mL) and acidified with conc. HCl until no more white solid precipitated. The mixture is extracted with ethyl acetate (2×8 mL) and the combined organic layers are concentrated in vacuo to give product (286) as white solid (60 mg, 95%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in water (1.5 mL)
  3. customprecipitated
  4. extractionThe mixture is extracted with ethyl acetate (2×8 mL)
  5. concentrationthe combined organic layers are concentrated in vacuo

Sources & evidence

ORD record
ord-b8de215eefe642f09f6a76990cba91e4
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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