Methyl 1-acetamido-4-oxocyclohexanecarboxylate → Methyl 1-acetamido-4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Methyl 1-acetamido-4-oxocyclohexanecarboxylate	HCID 10584690	—
Reactant	(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate	HCID 71698666	—
Product	Methyl 1-acetamido-4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate	HCID 86692399	—
Product	1-Acetamido-4-oxocyclohexanecarboxylate	HCID 86692400	—

Reaction Steps

The title compound was prepared following the procedure described on step 6 of method 2 for the preparation of intermediate 1, using methyl 1-acetamido-4-oxocyclohexanecarboxylate, as the reactant. 1-acetamido-4-oxocyclohexanecarboxylate was prepared following the procedures described in Journal of Chem. Soc., Perkin Trans. I, 1999, pp. 3375-3379. (84.0% yield), MS: m/e 346.1 (M+H)+, 2.213 min (method ?). 1H NMR (400 MHz, CHLOROFORM-d) δ 6.24 (s, 1H), 5.69 (td, J=3.3, 1.4 Hz, 1H), 3.82-3.58 (m, 3H), 2.87-2.67 (m, 1H), 2.61-2.44 (m, 2H), 2.42-2.33 (m, 2H), 2.19-2.07 (m, 1H), 2.01-1.94 (m, 3H). 19F NMR (376 MHz, CHLOROFORM-d) δ −74.02 (s, 3F).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906889B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-6dac3a43d4624a0c8c27b9f58b469fc7
Source note	uspto-grants-2014_12