Phosphorus oxychloride → HCID 86667598, compound

HRID 85315Notes

Reaction equation

HRID 85315 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH2:20][NH:21][CH2:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:31]([O-])(=[O:33])C.[Na+]>CN(C=O)C>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH2:20][NH:21][CH2:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:27])([CH3:29])[CH3:28])[CH:17]=[CH:18][C:19]=1[CH:31]=[O:33])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 680091752,2-Dimethylpropionic acid 2-[(3-benzyloxyphenyl)methylamino]ethyl ester

Product 1

HCID 86667598HCID 86667598, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

POCl3 (3.6 g, 23.4 mmol) was added to 20 ml of DMF in an ice bath. After 40 minutes, 2,2-dimethylpropionic acid 2-[(3-benzyloxyphenyl)methylamino]ethyl ester (8.0 g, 23.4 mmol) dissolved in DMF (10 ml) was added dropwise. The mixture was stirred for 16 hours. After an aqueous sodium acetate solution (20%, 100 ml) was added dropwise, the oily matter was subjected to extraction with ethyl acetate. Washing was performed with a saturated aqueous NaHCO3 solution (100 ml) and then with a saturated saline solution (100 ml). After drying over Na2SO4 and concentration, the residue was purified by silica gel chromatography to give a light yellow crystal (yield: 7.2 g (83.6%)).

Workup

  1. additionwas added dropwise
  2. extractionthe oily matter was subjected to extraction with ethyl acetate
  3. washWashing
  4. dry with materialAfter drying over Na2SO4 and concentration
  5. customthe residue was purified by silica gel chromatography
  6. customto give a light yellow crystal (yield: 7.2 g (83.6%))

Sources & evidence

ORD record
ord-3d0153f5afc94743b69d3e1e34f58aca
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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