Ethyl bromoacetate → HCID 57148517, compound

HRID 361922Notes

Reaction equation

HRID 361922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH2:23][C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[C:28]([C:33]#[N:34])[CH:27]=4)[CH2:21][OH:22])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]([CH2:21][OH:22])[CH2:23][C:24]3[N:25]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[C:28]([C:33]#[N:34])[CH:27]=4)=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 570293332-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propanol

Product 1

HCID 57148517HCID 57148517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propanol was dissolved in 30 ml of N,N-dimethylformamide. 280 mg of 60% sodium hydride was added to the above solution while stirring under ice cooling, and the stirring was continued for 20 minutes at the same temperature. The resulting reaction solution was mixed with 0.5 ml of ethyl bromoacetate, and the mixture was stirred for 1 hour. The thus treated reaction solution was mixed with an aqueous solution of ammonium chloride, extracted with a toluene/ethyl acetate mixture, washed with water, and then dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a dichloromethane/acetone mixture as an elution solvent. In this way, 1.5 g of the title compound was obtained in a viscous and oily form.

Workup

  1. customThe resulting reaction solution
  2. stirringthe mixture was stirred for 1 hour
  3. customThe thus treated reaction solution
  4. extractionextracted with a toluene/ethyl acetate mixture
  5. washwashed with water
  6. customdried
  7. distillationAfter distilling off the solvent
  8. customthe resulting residue was purified

Sources & evidence

ORD record
ord-e21447e8e65749169deb7e19afafd7ef
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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