Sodium Hydroxide → HCID 69332259, compound

HRID 354270Notes

Reaction equation

HRID 354270 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86587778HCID 86587778, compound

Product 1

HCID 69332259HCID 69332259, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the above ethyl (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoate was added MeOH (100 mL) and 1 N NaOH (50 mL). The mixture was stirred for 15 hr at room temp. After removal of MeOH under a reduced pressure, water (50 mL) was added to the residual solution. The aqueous solution was washed with Et2O (×2) and then acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc, washed with water, brine, dried over MgSO4 and evaporated in vacuo to afford 4.26 g (95%) (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoic acid as a crystalline solid.

Workup

  1. customAfter removal of MeOH under a reduced pressure, water (50 mL)
  2. additionwas added to the residual solution
  3. washThe aqueous solution was washed with Et2O (×2)
  4. additionacidified by the addition of 1 N HCl
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with water, brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-708d0322ca2e42d6a83d76664e074c92
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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