Triethylamine → 2-[(tert-Butoxy)carbonylamino]-N-(phenylmethoxy)acetamide

O-Benzylhydroxylamine hydrochloride (15.0 g, 93.8 mMol) was dissolved in methanol (150 ml) and added to a solution of potassium hydroxide (5.27 g, 93.8 mMol) in methanol (50 ml). The resulting mixture was cooled, filtered, evaporated, dissolved in tetrahydrofuran (25 ml) and filtered as solution A. t-Butyloxycarbonyl glycine (16.4 g, 93.8 mMol) was dissolved in tetrahydrofuran (75 ml), triethylamine (13.2 ml, 93.8 mMol) added and the solution cooled to -10° C. with dry ice/ethanol. Iso-butyl chloroformate (12.2 ml, 93.8 mMol) was added and the solution stirred cold 2 minutes, before adding solution A dropwise. The mixture was stirred cold 1 hour and at room temperature 2 hours, filtered, evaporated, dissolved in ethyl acetate (100 ml), washed with water (3× 50 ml), dried over magnesium sulfate and evaporated to an oil.

1. temperatureThe resulting mixture was cooled
2. filtrationfiltered
3. customevaporated
4. dissolutiondissolved in tetrahydrofuran (25 ml)
5. filtrationfiltered as solution A
6. stirringThe mixture was stirred cold 1 hour and at room temperature 2 hours
7. filtrationfiltered
8. customevaporated
9. dissolutiondissolved in ethyl acetate (100 ml)
10. washwashed with water (3× 50 ml)
11. dry with materialdried over magnesium sulfate
12. customevaporated to an oil

ORD record

ord-564b064ae6d147c3b71798fedd0fe5c9

Source dataset

uspto-grants-1977_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04028401