Ethyl 4-bromobutyrate → HCID 19809176, compound

HRID 373980Notes

Reaction equation

HRID 373980 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH:10][CH:11]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>CS(C)=O>[OH:10][CH:11]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 12541329HCID 12541329, compound

Product 1

HCID 19809176HCID 19809176, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

525 mg of ethyl 4-bromobutyrate were added to a solution of 574 mg of p-[2-[[(RS)-2-hydroxy-3-phenoxypropyl]-amino]ethyl]phenol and 300 mg of potassium t-butylate in 10 ml of dimethylsulfoxide and the mixture was stirred at room temperature under argon for 6 hours. The solvent was evaporated in vacuo and the residue was chromatographed on 75 g of silica gel. Utilizing chloroform/n-propanol/saturate ammonia (500:10:1), there were obtained 600 mg of pure, amorphous ethyl 4-[p-[2-[[(RS)-2-hydroxy-3-phenoxypropyl]amino]ethyl]phenoxy]butyrate, ε221 =17510.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on 75 g of silica gel
  3. concentrationUtilizing chloroform/n-propanol/saturate ammonia (500:10:1)

Sources & evidence

ORD record
ord-12c1713cd4994af4b7820518597ebe19
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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