Methanol → 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propionic acid

HRID 361920Notes

Reaction equation

HRID 361920 reaction equation
[OH-].[Na+].CO.[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH2:29][C:30]3[NH:31][C:32]4[C:37]([CH:38]=3)=[CH:36][CH:35]=[C:34]([C:39]#[N:40])[CH:33]=4)[C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>O>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH2:29][C:30]3[NH:31][C:32]4[C:37]([CH:38]=3)=[CH:36][CH:35]=[C:34]([C:39]#[N:40])[CH:33]=4)[C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 56998289HCID 56998289, compound

Product 1

HCID 571914662-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propionic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous solution containing 3 g of sodium hydroxide dissolved in 10 ml of water was added to 100 ml of a methanol solution containing 22 g of methyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propionate, and the resulting mixture was stirred at room temperature for 24 hours. After distilling off the solvent, the remaining portion was adjusted to pH 4-5 with citric acid and then extracted with ethyl acetate. By drying the extract to distill off the solvent, 20 g of 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propionic acid was obtained.

Workup

  1. distillationAfter distilling off the solvent
  2. extractionextracted with ethyl acetate
  3. customBy drying the
  4. extractionextract
  5. distillationto distill off the solvent

Sources & evidence

ORD record
ord-c39376c190a04330a45b19141c6c681c
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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