Triethylamine → Carbamic acid, [2-[hexahydro-4-(3-phenylpropyl)-1H-1,4-diazepin-1-yl]-2-oxoethyl]-, 1,1-dimethylethyl ester

To a suspension of 2.8 g (15.98 mmol.) of N-tert-butoxycarbonyl glycine and 3.67 g (23.96 mmol.) of 1-hydroxybenzotriazole monohydrate was added, at room temperature, 4.6 g (24.0 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride. The mixture was stirred for one hour. To the reaction system, was added an acetonitrile solution (20 ml) of 5.65 (16.99 mmol.) of 1-(3-phenylpropan-1-yl)-2,3,5,6-tetrahydro-7H-1,4-diazepine dihydrochloride, 5.17 g (33.96 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 2.3 ml (16.5 mmol.) of triethylamine. The mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The crude product thus-obtained was purified by means of a column chromatography (methanol/ethyl acetate 10-20%). The solvent was distilled off under reduced pressure to afford the object compound as a pale yellow oily product. The yield was 5.64 g (94%).

1. additionwas added, at room temperature
2. stirringThe mixture was stirred for 2 hours
3. distillationThe solvent was distilled off under reduced pressure
4. additionTo the residue was added water, which
5. extractionwas subjected to extraction with ethyl acetate
6. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
7. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
8. distillationby distilling off the solvent under reduced pressure

ORD record

ord-e02e7f5a006d44ed90cf36b810399b29

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235731B1