Stannous chloride dihydrate → HCID 69317243, compound

Temperature

60 °C

The 5-nitrotryptophan methyl ester intermediate of example 47 (0.400 g, 0.72 mmol) was dissolved in DMF (3 mL). Water (0.1 mL) and tin dichloride dihydrate (0.812 g, 3.6 mmol) were added and the mixture heated at 60° C. for 3 h and stirred overnight at room temperature. The reaction mixture was diluted with water (50 mL), saturated aqueous NaHCO3 (20 mL) and EtOAc (50 mL). The mixture was vigorously stirred for 5 min and filtered to remove solids (wash cake with 50 mL of EtOAc). The organic layer from the filtrate was washed with water (3×50 mL) and brine (50 mL), and subsequently dried over MgSO4. Volatiles were removed under reduced pressure and the residue was triturated with TBME (10 mL) to give the 5-aminotryptophan methyl ester derivative as a white solid (0.250 g).

1. stirringThe mixture was vigorously stirred for 5 min
2. filtrationfiltered
3. customto remove
4. washsolids (wash cake with 50 mL of EtOAc)
5. washThe organic layer from the filtrate was washed with water (3×50 mL) and brine (50 mL)
6. dry with materialsubsequently dried over MgSO4
7. customVolatiles were removed under reduced pressure
8. customthe residue was triturated with TBME (10 mL)

ORD record

ord-29fa201a2cf84b278a22530c962a862e

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448281B1