Isopropylamine → HCID 10729350, compound

To a solution of N-Cbz-glycine (20.9 g, 100 mmol) in THF (400 mL) at 0° C. was added N-methylmorpholine (NMM) (12.1 mL, 110 mmol) and i-butylchloroformate (13 mL, 100 mmol). The resultant mixture was stirred at 0° C. for 2 min and then i-propylamine (9.4 mL, 110 mmol) was added. The reaction mixture was warmed to room temperature and stirred at this temperature for 16 h. The mixture was filtered through a pad of CELITE™ and concentrated in vacuo. The crude residue was dissolved in ethyl acetate (500 mL) and washed with 1N HCl (aq.) (1×100 mL), sat. NaHCO3 (aq.) (1×100 mL) and brine (1×100 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford (isopropylcarbamoylmethyl)carbamic acid benzyl ester as a white solid (24.5 g, 98 mmol, 98%) which was used without further purification in the next reaction.

1. filtrationThe mixture was filtered through a pad of CELITE™
2. concentrationconcentrated in vacuo
3. dissolutionThe crude residue was dissolved in ethyl acetate (500 mL)
4. washwashed with 1N HCl (aq.) (1×100 mL), sat. NaHCO3 (aq.) (1×100 mL) and brine (1×100 mL)
5. dry with materialThe organic layer was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-2a20c28a52be4db68c35a46fe747a67d

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807686B2