L-Tyrosine → HCID 3478588, compound

HRID 1056867Notes

Reaction equation

HRID 1056867 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]([C:15]([OH:17])=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[O-]S([O-])(=O)=O.[Ca+2].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].[C:35](OCC)(=O)C>CO>[CH2:28]([O:27][C:25]([NH:5][CH:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[C:15]([O:17][CH3:35])=[O:16])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 6057L-TyrosineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 24497Calcium Sulfate

Product 1

HCID 3478588HCID 3478588, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (4.6 mL, 63.33 mmol, 2 eq) was added dropwise to dry MeOH (65 mL) at 0° C. and stirred for 5 min. Tyrosine (5.70 g, 31.5 mmol, 1 eq) was then added and the reaction vessel was fitted with a drying tube filled with drierite and slowly allowed to come to room temperature over 21 h. The solvent was then evaporated and crude product dried over high vacuum for 8 h. The crude product was then dissolved in a 1:1 mixture of acetone (63 mL) and a 7% solution of Na2CO3 in water (63 mL). Benzyl chloroformate (4.7 mL, 34.7 mmol, 1.2 eq) was then added dropwise and the reaction was stirred for 3 h at room temperature. Ethyl acetate was then added (300 mL), and the organic layer was washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The solvent was evaporated to give 10 as a viscous yellow oil (10.37 g). The product was used in the next step without purification.

Workup

  1. customthe reaction vessel was fitted with a drying tube
  2. waitto come to room temperature over 21 h
  3. customThe solvent was then evaporated
  4. customcrude product dried over high vacuum for 8 h
  5. dissolutionThe crude product was then dissolved in a 1:1 mixture of acetone (63 mL)
  6. stirringthe reaction was stirred for 3 h at room temperature
  7. washthe organic layer was washed with water (100 mL), brine (100 mL)
  8. dry with materialdried over Na2SO4
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-abd693769b8c4beb856b3ee6c57dd9f0
Source dataset
uspto-grants-2016_07
Patent number
US09399653B2

Reaction notes

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