Tyrosol → HCID 70157854, compound

HRID 1936745Notes

Reaction equation

HRID 1936745 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]CO)=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH:14]([NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=[O:32].[Cs+].[Cs+]>C(#N)C>[OH:32][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:12][CH2:13][C@@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 10796Cesium carbonateHCID 15857342HCID 15857342, compound

Product 1

HCID 70157854HCID 70157854, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture constituted by 690 mg of 4-hydroxybenzenethanol, 1.72 g of ethyl 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]butanoate and 1.63 g of Cs2CO3 in 100 ml of acetonitrile is heated under reflux or 45 minutes, the solid is filtered, washed with dichloromethane then the filtrate is evaporated under reduced pressure until 2.6 g of crude product is obtained which is purified by chromatography on a silica column (Kieselgel 60; 40-63 μm) eluting with a dichloromethane/methanol mixture 9/5. 1.58 g of expected product is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux or 45 minutes
  3. filtrationthe solid is filtered
  4. washwashed with dichloromethane
  5. customthe filtrate is evaporated under reduced pressure until 2.6 g of crude product
  6. customis obtained which
  7. customis purified by chromatography on a silica column (Kieselgel 60; 40-63 μm)
  8. washeluting with a dichloromethane/methanol mixture 9/5

Sources & evidence

ORD record
ord-2a3a04d2948e49399d304c9db6f3774a
Source dataset
uspto-grants-2002_05
Patent number
US06391904B1

Reaction notes

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