Cesium carbonate → HCID 70158418, compound

HRID 1936744Notes

Reaction equation

HRID 1936744 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH:15]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:14][C@@H:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 824523-(4-Hydroxyphenyl)propanolHCID 15857342HCID 15857342, compound

Product 1

HCID 70158418HCID 70158418, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture constituted by 306 mg of 4-hydroxybenzenepropanol, 770 mg of ethyl 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]butanoate and 740 mg of Cs2CO3 in 10 ml of acetonitrile is heated under reflux for 45 minutes, the solid is filtered, washed with dichloromethane then the filtrate is evaporated under reduced pressure until 1.5 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 95/5. 440 mg of expected product is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 45 minutes
  3. filtrationthe solid is filtered
  4. washwashed with dichloromethane
  5. customthe filtrate is evaporated under reduced pressure until 1.5 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 95/5

Sources & evidence

ORD record
ord-1e48bb9b41814a59914791a66702d168
Source dataset
uspto-grants-2002_05
Patent number
US06391904B1

Reaction notes

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