Methanol → HCID 20793230, compound

HRID 1070364Notes

Reaction equation

HRID 1070364 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[NH:15][C@H:16]([C:18]([OH:20])=[O:19])[CH3:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:25]O>>[CH3:25][O:19][C:18](=[O:20])[C@H:16]([CH3:17])[NH:15][C:13]1[C:12]2[C:7]([CH:6]=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 18658556HCID 18658556, compound

Product 1

HCID 20793230HCID 20793230, compoundYield 68%

Conditions

Temperature
0 °C

Procedure

0.7 g of 9-anthryl alanine was mixed with 20 ml of anhydrous methanol, cooled to 0° C. 1.5 eq of thionyl chloride was added drop-wise, refluxing overnight. The solvent was removed on a rotary evaporator. The crude product was dissolved in ethyl acetate. The organic phase was washed by 5% of sodium bicarbonate, distilled water, and dried by anhydrous sodium carbonate. The solvent was removed on a rotary evaporator. The product was purified by column chromatography (hexane: ethyl acetate=1:2.5). 0.5 g of oil-like yellow solid was obtained. The yield was 68%. The product decomposes at 180° C.

Workup

  1. temperaturerefluxing overnight
  2. customThe solvent was removed on a rotary evaporator
  3. dissolutionThe crude product was dissolved in ethyl acetate
  4. washThe organic phase was washed by 5% of sodium bicarbonate
  5. distillationdistilled water
  6. dry with materialdried by anhydrous sodium carbonate
  7. customThe solvent was removed on a rotary evaporator
  8. customThe product was purified by column chromatography (hexane: ethyl acetate=1:2.5)

Sources & evidence

ORD record
ord-edfa02e0f17345adad241813210c37d8
Source dataset
uspto-grants-2005_06
Patent number
US06902720B2

Reaction notes

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