Phenylacetyl chloride → HCID 86606782, compound

HRID 217953Notes

Reaction equation

HRID 217953 reaction equation
Cl.[CH:2]([NH:5][C@@H:6]([CH3:9])[CH2:7][OH:8])([CH3:4])[CH3:3].[C:10]1([CH2:16][C:17]([Cl:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[ClH:19].[CH:2]([NH:5][C@@H:6]([CH3:9])[CH2:7][O:8][C:17](=[O:18])[CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 86606784HCID 86606784, compound

Product 1

HCID 86606782HCID 86606782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10 g of (S)-2-isopropylamino-propan-1-ol hydrochloride in 300 ml of dichloromethane 10 ml of phenylacetic acid chloride are added. The reaction mixture is stirred at RT for about 15 h and then substantially concentrated under reduced pressure, and the highly viscous residue is partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase is washed with water, dried over sodium sulfate and concentrated. The resin-like residue is purified by silica gel chromatography, and the product fraction is separated off and concentrated. The residue is dissolved in 150 ml of 2-propanol and 25 ml 2 N HCl in water are added. The mixture is stirred for about 15 h and the resulting crystals are filtered off. This gives 10.9 g of the title compound. M. p. 114-118° C. (unsharp)

Workup

  1. additionare added
  2. concentrationsubstantially concentrated under reduced pressure
  3. customthe highly viscous residue is partitioned between dichloromethane and saturated sodium bicarbonate solution
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resin-like residue is purified by silica gel chromatography
  8. customthe product fraction is separated off
  9. concentrationconcentrated
  10. dissolutionThe residue is dissolved in 150 ml of 2-propanol
  11. addition25 ml 2 N HCl in water are added
  12. stirringThe mixture is stirred for about 15 h
  13. filtrationthe resulting crystals are filtered off

Sources & evidence

ORD record
ord-8a7b33d0b1c641d09919545ded979e53
Source dataset
uspto-grants-2012_06
Patent number
US08198295B2

Reaction notes

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