Ethanol → (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Ethylamine	HCID 6341	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamide	HCID 10495486	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate	HCID 59201513	34%

Reaction Steps

To a solution of (S)-tert-butyl 3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (1.17 g, 4.3 mmol) and TEA (2.4 mL, 17.2 mmol) in anhydrous DMF was added 2.0 M EtNH2 solution in EtOH (6.5 mL, 13 mmol), followed by HBTU (1.96 g, 5.2 mmol). The resulting solution was stirred at rt for 3 h. The reaction was concentrated under reduced pressure and the residue dissolved in EtOAc (50 mL). The mixture was then washed with 1 M NaOH (4 times), 1 M HCl (3 times), sat. aq. NaHCO3, brine, dried over Na2SO4 and filtered. The concentrated residue gave (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate (444 mg, 34%). MS ESI +ve m/z 299 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487108B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-9fd7a120d1f64e0ca54472952a0890d1
Source note	uspto-grants-2013_07