2-Bromoethanol → HCID 86629018, compound

HRID 1013437Notes

Reaction equation

HRID 1013437 reaction equation
[NH2:1][C@H:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Br[CH2:19][CH2:20][OH:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[OH:21][CH2:20][CH2:19][NH:1][C@@H:2]([CH2:3][C:4]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:5])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 7269469D-aspartic acid di-t-butyl ester

Product 1

HCID 86629018HCID 86629018, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of di-tert-butyl L-aspartate (5.62 g-20 mmol), 2-bromoethanol (2.84 ml-40 mmol) and K2CO3 (5.6 g-40 mmol) in 100 ml of acetonitrile is heated at reflux for 16 hours. The mineral salts are filtered off and the solvent is removed by distillation in vacuo. The crude product so obtained is purified by flash chromatography on silica gel using a (95/5) dichloromethane/ethanol mixture as eluant. The expected product is obtained in the form of a colourless oil.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationThe mineral salts are filtered off
  3. customthe solvent is removed by distillation in vacuo
  4. customThe crude product so obtained
  5. customis purified by flash chromatography on silica gel using a (95/5) dichloromethane/ethanol mixture as eluant

Sources & evidence

ORD record
ord-3d01342a0d654d76a4bdc76d6348a218
Source dataset
uspto-grants-2011_07
Patent number
US07981920B2

Reaction notes

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