Ethyl chloroacetate → HCID 55288043, compound

HRID 2366348Notes

Reaction equation

HRID 2366348 reaction equation
[H-].[Na+].[NH2:3][C@@H:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][OH:6].Cl[CH2:11][C:12](OCC)=[O:13]>C1(C)C=CC=CC=1>[CH:7]([C@@H:4]1[NH:3][C:12](=[O:13])[CH2:11][O:6][CH2:5]1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 640993L-Valinol

Product 1

HCID 55288043HCID 55288043, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To an ice-cold, stirred suspension of sodium hydride (2.59 g, 64.8 mmol) in toluene (90 mL) was added dropwise a solution of (S)-2-amino-3-methylbutan-1-ol (3 g, 29.1 mmol) in toluene (60 mL). The reaction was then warmed to room temperature and a solution of ethyl chloroacetate (3.56 g, 29.1 mmol) in toluene (16 mL) was added dropwise. The resulting mixture was heated to reflux for 20 h under nitrogen and then concentrated under vacuum. The residue was purified by flash chromatography to afford 2.8 g of product (MS: (M+H)=144.3).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 20 h under nitrogen
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-470b20a384fb445c88e5363b5a6f05e1
Source dataset
uspto-grants-2014_04
Patent number
US08697739B2

Reaction notes

Loading…