Dichloromethane → 256477-33-5

N-Berzylglycine t-butyl ester ##STR118## A solution of t-butyl bromoacetate (1.5 mL, 10.1 mmol) in CH2Cl2 (10 mL) was added dropwise to a stirred solution of benzylamine (10.9 mL, 100 mmol) in CH2Cl2 (40 mL) at 0° C., the mixture was stirred for 1 h and then warmed to room temperature and stirred for an additional 3 d. The mixture was washed with water (3×50 mL), dilute HCl (1 N) and the combined aqueous washings were extracted with Et2O. The organic phase was washed with saturated aqueous NaHCO3, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in Et2O, treated with a solution of HCl in ether (0.5 M) and the resulting precipitate was collected and dissolved in EtOAc. This solution was filtered through hyflo, and partially evaporated in vacuo to give a thick slurry. The solid was collected by filtration, washed with Et2O and then dried to give N-benzylglycine t-butyl ester hydrochloride (1.03 g, 4.00 mmol) as a white solid.

1. stirringstirred for an additional 3 d
2. washThe mixture was washed with water (3×50 mL), dilute HCl (1 N)
3. extractionthe combined aqueous washings were extracted with Et2O
4. washThe organic phase was washed with saturated aqueous NaHCO3
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo
7. dissolutionThe residue was dissolved in Et2O
8. additiontreated with a solution of HCl in ether (0.5 M)
9. customthe resulting precipitate was collected
10. dissolutiondissolved in EtOAc
11. filtrationThis solution was filtered through hyflo
12. custompartially evaporated in vacuo
13. customto give a thick slurry
14. filtrationThe solid was collected by filtration
15. washwashed with Et2O
16. customdried

ORD record

ord-ed56b83ee8e2484aa13971b7e5eb0274

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093731