Benzaldehyde → HCID 22885226, compound

HRID 1418796Notes

Reaction equation

HRID 1418796 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH:8][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

Product 1

HCID 22885226HCID 22885226, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.9 g (71.5 mmol) of tyrosine-tert-butyl ester and 8.33 g (78.6 mmol) of benzaldehyde are stirred in 50 ml of methanol for 3 hours at 24° C. and then mixed with 3.37 g (53.6 mmol) of sodium cyanoborohydride. After 24 hours of stirring at room temperature, the batch is adjusted to pH 2 by careful addition of semiconcentrated hydrochloric acid, then neutralized with concentrated aqueous sodium bicarbonate solution and after substantial evaporation of methanol with ethyl acetate, it is shaken out. The organic phase is dried on anhydrous magnesium sulfate, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine; the product-containing fractions are combined and concentrated by evaporation.

Workup

  1. customafter substantial evaporation of methanol with ethyl acetate, it
  2. stirringis shaken out
  3. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cd18d88b887e40928d04f77e91d10557
Source dataset
uspto-grants-1999_03
Patent number
US05885548

Reaction notes

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