Tyrosine Methyl Ester → HCID 86606582, compound

HRID 1866196Notes

Reaction equation

HRID 1866196 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[S-:13][C:14]#[N:15].[Na+].[CH3:17][O:18][C:19](=[O:30])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[NH2:21]>C(O)C>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([C:3]2[N:15]=[C:14]([NH:21][C@@H:20]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[C:19]([O:18][CH3:17])=[O:30])[S:13][CH:2]=2)=[CH:6][CH:7]=1)#[N:10]

Participants

5

Reactant 3

HCID 70652Tyrosine Methyl EsterHCID 986544-(Bromoacetyl)benzonitrileHCID 516871Sodium thiocyanate

Product 1

HCID 86606582HCID 86606582, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

22.3 g (0.1 mol) of 4-(bromoacetyl)benzonitrile and 8.66 g (0.107 mol) of dry sodium thiocyanate in ethanol (200 ml) were stirred for 3 h at 50° C. Then 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 (SiO2, ethyl acetate/hexane). The yield was 53%. MS (ES) 379 (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-577e8b12d4994bafb0fbd9664d15d54a
Source dataset
uspto-grants-2009_12
Patent number
US07629370B2

Reaction notes

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