Tyrosine Methyl Ester → HCID 86606583, compound

HRID 970089Notes

Reaction equation

HRID 970089 reaction equation
Br[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)O.[S-:12][C:13]#[N:14].[Na+].[CH3:16][O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH2:20]>C(O)C>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:13]([NH:20][C@@H:19]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[C:18]([O:17][CH3:16])=[O:29])[S:12][CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70652Tyrosine Methyl EsterHCID 516871Sodium thiocyanateHCID 15323920HCID 15323920, compound

Product 1

HCID 86606583HCID 86606583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

21.2 g (0.1 mol) of 2-bromo-1-(4-methylphenyl)ethanol 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 then 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 (SiO2, ethyl acetate/hexane). The yield was 17.67 g (48%). MS (ES) 368 (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 (SiO2, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d3b85d5b03b548058858802086c38c14
Source dataset
uspto-grants-2007_12
Patent number
US07309791B2

Reaction notes

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