cis-1,2-Cyclohexanedicarboxylic acid → Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidinium]-5,6-dione cis-2-carboxycyclohexanecarboxylate

HRID 1665269Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[C@@H:22]1([C:31]([OH:33])=[O:32])[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[C:28]([OH:30])=[O:29]>C(#N)C>[C:31]([C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]1[C:28]([O-:30])=[O:29])([OH:33])=[O:32].[NH2+:1]1[CH2:2][CH2:3][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.5 g, 1.66 mmol) and acetonitrile (20 ml) which had been preheated to 80° C. was added a preheated (80° C.). solution of cis-cyclohexane-1,2-dicarboxylic acid (0.286 ml, 1.66 mmol) in acetonitrile (20 ml). The reaction mixture was stirred overnight at 80° C. The resulting purple precipitate was filtered, washed with acetonitrile, and dried under reduced pressure to afford the product as a purple solid (0.472 g, 60%). M.p.=204-207° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.90-7.87 (m, 1H), 7.83-7.81 (m, 1H), 7.78-7.73 (m, 1H), 7.58-7.54 (m, 1H), 3.16-3.11 (m, 4H), 3.07-3.00 (m, 2H), 2.53-2.48 (m, 2H), 2.11-2.05 (m, 2H), 1.88-1.75 (m, 4H), 1.52-1.40 (m, 4H), 1.33-1.29 (m, 2H); LCMS: 302 [M+H].

Workup

customhad been preheated to 80° C.
additionwas added a preheated (80° C.)
filtrationThe resulting purple precipitate was filtered
washwashed with acetonitrile
customdried under reduced pressure

Sources & evidence

ORD record: ord-9db75ff9b4ad485f8e582245d93caea8
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039503B2

Reaction notes

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