Benzylamine → N-Benzyl 2-(Carbobenzyloxyamino)-3-Methoxypropionamide

A solution of 11 (0.52 g, 2.04 mmol) in dry tetrahydrofuran (10 mL) was cooled to −78° C. in a dry ice-acetone bath under a N2 atmosphere. To this was added via a dry syringe 4-methylmorpholine (0.34 mL, 3.06 mmol). After stirring for 5 minutes, isobutyl chloroformate (0.4 mL, 3.06 mmol) was added via dry syringe and then the mixture stirred for 5 minutes. This was followed by the addition of benzylamine (0.32 mL, 3.06 mmol). After stirring at −78° C. for 5 minutes, the reaction was allowed to warm to room temperature, and stirring was continued at room temperature (30 min). The hydrochloride salt of 4-methyl morpholine was removed from the reaction by filtration. The clear filtrate was evaporated in vacuo and the residue was triturated with ethyl ether (5.0 mL). The white crystalline product obtained was isolated by filtration after washing with small amounts of ether and air-dried (0.55 g, 78%): mp 112°-114° C., Rf 0.6 (10% MeOH/CHCl3)

1. customvia dry syringe
2. stirringthe mixture stirred for 5 minutes
3. stirringAfter stirring at −78° C. for 5 minutes
4. stirringstirring
5. customwas continued at room temperature
6. custom(30 min)
7. customThe hydrochloride salt of 4-methyl morpholine was removed from the reaction by filtration
8. customThe clear filtrate was evaporated in vacuo
9. customthe residue was triturated with ethyl ether (5.0 mL)
10. customThe white crystalline product obtained
11. customwas isolated by filtration
12. washafter washing with small amounts of ether
13. customair-dried (0.55 g, 78%)

ORD record

ord-ce0a20d96aa04cbe8878ab16f826c0c8

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE038551E1