2-Chloroacetophenone → HCID 86606580, compound

HRID 970084Notes

Reaction equation

HRID 970084 reaction equation
[CH2:1](Cl)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[S-:11][C:12]#[N:13].[Na+].[CH3:15][O:16][C:17](=[O:28])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[NH2:19]>C(O)C>[OH:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][C@H:18]([NH:19][C:12]2[S:11][CH:1]=[C:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:13]=2)[C:17]([O:16][CH3:15])=[O:28])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 107572-ChloroacetophenoneHCID 70652Tyrosine Methyl EsterHCID 516871Sodium thiocyanate

Product 1

HCID 86606580HCID 86606580, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.40 g (0.1 mol) of phenacyl chloride and 8.66 g (0.107 mol) of dry sodium thiocyanate in ethanol (200 ml) were stirred for 3 h at 50° C. The solution of 19.51 g (0.1 mol) of (S)-tyrosine methyl ester in ethanol (100 ml) was added in one portion and the reaction mixture was stirred for 12 h. After removing ethanol by distillation, water and ethyl acetate were added. Aqueous phase was extracted twice with ethyl acetate, combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The product was purified by chromatography. The yield was 20.54 g (58%). MS (ES) 354 (M+, 100%)

Workup

  1. customAfter removing ethanol
  2. distillationby distillation, water and ethyl acetate
  3. additionwere added
  4. extractionAqueous phase was extracted twice with ethyl acetate
  5. dry with materialwere dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-f2d19daa31924082a86f3a54e045ecf4
Source dataset
uspto-grants-2007_12
Patent number
US07309791B2

Reaction notes

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