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

HRID 1401039Notes

Reaction equation

HRID 1401039 reaction equation
[F:1][C:2]([F:48])([F:47])[S:3](OC1C(C)(C)[C@H]2[C@](C)(CC=1)[C@@H]1[C@](C)([C@@]3(C)[C@H](CC1)[C@H]1[C@H](C(C)=C)CC[C@]1(NCCN1CCS(=O)(=O)CC1)CC3)CC2)(=[O:5])=[O:4].[C:49]([NH:52][C:53]1([C:60]([O:62][CH3:63])=[O:61])[CH2:58][CH2:57][C:56](=[O:59])[CH2:55][CH2:54]1)(=[O:51])[CH3:50]>>[C:49]([NH:52][C:53]1([C:60]([O:62][CH3:63])=[O:61])[CH2:54][CH2:55][C:56]([O:59][S:3]([C:2]([F:48])([F:47])[F:1])(=[O:5])=[O:4])=[CH:57][CH2:58]1)(=[O:51])[CH3:50].[C:49]([NH:52][C:53]1([C:60]([O-:62])=[O:61])[CH2:54][CH2:55][C:56](=[O:59])[CH2:57][CH2:58]1)(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 10584690Methyl 1-acetamido-4-oxocyclohexanecarboxylateHCID 71698666(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

Product 2

HCID 86692399Methyl 1-acetamido-4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylateHCID 866924001-Acetamido-4-oxocyclohexanecarboxylate

Procedure

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).

Workup

  1. customm/e 346.1 (M+H)+, 2.213 min (method ?)

Sources & evidence

ORD record
ord-6dac3a43d4624a0c8c27b9f58b469fc7
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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