Ethyl bromoacetate → HCID 63303097, compound

HRID 1855587Notes

Reaction equation

HRID 1855587 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][NH:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1)[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

HCID 63303097HCID 63303097, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl 3-aminoazetidine-1-carboxylate (10.0 g, 58 mmol), ethyl 2-bromoacetate (10.7 g, 64 mmol) and potassium carbonate (24.0 g, 174 mmol) in MeCN (200 mL) was stirred at rt for 13 hrs. The reaction mixture was filtered and concentrated. The crude material was purified by silica gel column chromatography (gradient elution 0-66% EtOAc/petroleum ether) to afford tert-butyl 3-(2-ethoxy-2-oxoethylamino)azetidine-1-carboxylate (12.1 g, 81%) as a white solid. ESI-MS (EI+, m/z): 259.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude material was purified by silica gel column chromatography (gradient elution 0-66% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-ca4c9be5dae347fc8b8cd3fb7f04135e
Source dataset
uspto-grants-2015_02
Patent number
US08962844B2

Reaction notes

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