Ethyl bromoacetate → 4-Ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

HRID 400455Notes

Reaction equation

HRID 400455 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([CH:12]1[C:18](=[O:19])[CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13]1)=[O:11])[CH3:8].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C=O)C.O>[CH2:7]([O:9][C:10]([C:12]1([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:18](=[O:19])[CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Product 1

HCID 866860534-Ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl esterYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6.7 g potassium carbonate was added to 7 g 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester in 50 mL DMF and stirred at RT. After 30 min 6.1 g ethyl bromoacetate was added and the reaction was stirred at RT over night. The reaction was diluted with water and extracted with ethyl acetate/hexane (1/1). The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography on silica gel (15% ethyl acetate in hexane) to give 5.6 g of the desired product.

Workup

  1. stirringthe reaction was stirred at RT over night
  2. extractionextracted with ethyl acetate/hexane (1/1)
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-75e96e8ed98d401891547c25d5ec51d8
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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