Sodium Hydroxide → 2-{2-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-isoindol-1-yl}acetic acid

HRID 1592768Notes

Reaction equation

HRID 1592768 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:17][C:18]([O:20]C)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:17][C:18]([OH:20])=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58777840tert-Butyl 1-(2-methoxy-2-oxoethyl)isoindoline-2-carboxylate

Product 1

HCID 587778602-{2-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-isoindol-1-yl}acetic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-methoxycarbonylmethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (52.6 g, 180.5 mmol) in MeOH (500 mL) was added 1 N NaOH (199 mL, 199.0 mmol). The mixture is stirred at r.t. for about 48 hours and then concentrated to dryness. The resulting residue was dissolved in water (300 mL) and extracted with diethyl ether (2×). The aqueous portion was acidified to pH 2 with 10% aqueous sodium bisulfate and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated to dryness to afford about 49.8 g of the final compound (99%). EIS-MS 276 [M−1].

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was dissolved in water (300 mL)
  3. extractionextracted with diethyl ether (2×)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fb5da9fc9307488ca921fd3c3d90f3bc
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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