Sodium Carbonate → HCID 22940769, compound

HRID 1459118Notes

Reaction equation

HRID 1459118 reaction equation
[CH:1]1[CH:6]=[C:5]([CH2:7][CH:8]([NH2:12])[C:9]([OH:11])=[O:10])[C:4]([OH:13])=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[C:18](=O)([O-])[O-].[Na+].[Na+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CO>[CH3:18][O:10][C:9](=[O:11])[C@H:8]([CH2:7][C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[OH:13])[NH:12][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 91482DL-o-Tyrosine

Product 1

HCID 22940769HCID 22940769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.5 g (52.4 mmol) of o-tyrosine (2-hydroxyphenylalanine, Heraeus) is suspended in 48 ml of methanol, cooled in an ice bath and mixed drop by drop with 7.6 ml (105 mmol) of thionyl chloride. After one hour, the batch is heated to reflux temperature and stirred for three hours. Then, it is allowed to stir overnight at room temperature. It is evaporated to dryness, the residue is taken up in methanol, concentrated by evaporation and the process is repeated twice. It is taken up in 50 ml of water, adjusted to pH 8.5 with 1.5 molar sodium carbonate solution and 22.1 ml (63 mmol) of benzyl chloroformate is added under pH control. It is stirred for four hours at room temperature, the organic phase is separated, it is washed with water and dried on sodium sulfate. After the concentration by evaporation, the residue is chromatographed on silica gel (methylene chloride/ethyl acetate).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe batch is heated
  3. temperatureto reflux temperature
  4. stirringto stir overnight at room temperature
  5. customIt is evaporated to dryness
  6. concentrationconcentrated by evaporation
  7. additionis added under pH control
  8. stirringIt is stirred for four hours at room temperature
  9. customthe organic phase is separated
  10. washit is washed with water
  11. customdried on sodium sulfate
  12. concentrationAfter the concentration
  13. customby evaporation
  14. customthe residue is chromatographed on silica gel (methylene chloride/ethyl acetate)

Sources & evidence

ORD record
ord-6cf6c9d006d74ee48f8a36a2401a8344
Source dataset
uspto-grants-1998_12
Patent number
US05853699

Reaction notes

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