Potassium Iodide → HCID 11014455, compound

HRID 1614758Notes

Reaction equation

HRID 1614758 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@H:8]([NH:12][C:13](=[O:22])[C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:25]([CH2:24][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@H:8]([NH:12][C:13](=[O:22])[C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1)([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10108652HCID 10108652, compound

Product 1

HCID 11014455HCID 11014455, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.8 g of N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-mandelamide, obtained according to Example 3(b), 7.1 ml of ethyl bromoacetate, 22 g of anhydrous potassium carbonate and 1 g of potassium iodide in 600 ml of anhydrous acetone, is heated with reflux and with stirring for 5 hours and a half. The reaction mixture is filtered, evaporated to dryness and the oil which separates is left to crystallize. The solid so obtained is purified by flash-chromatography (elution with a 1/1 mixture of ethyl acetate/cyclohexane). The solid on the column is taken up and treated with 20 ml of ethyl ether, filtered and crystallized from ethyl acetate to give 11.5 g of N-[(2S)-7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-mandelamide, SR 58638; m.p. 115°-117° C.; [alpha]=-98.3° (methanol, c=1%). Yield: 57%.

Workup

  1. customobtained
  2. temperatureis heated
  3. temperaturewith reflux
  4. filtrationThe reaction mixture is filtered
  5. customevaporated to dryness
  6. waitthe oil which separates is left
  7. customto crystallize
  8. customThe solid so obtained
  9. customis purified by flash-chromatography (
  10. washelution
  11. additionwith a 1/1 mixture of ethyl acetate/cyclohexane)
  12. additiontreated with 20 ml of ethyl ether
  13. filtrationfiltered
  14. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8a49b35b93aa4d45b0a7de944b28cfa7
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

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