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

HRID 1665270Notes

Reaction equation

HRID 1665270 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: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

3

Reactant 2

HCID 720895(1R,2R)-(-)-1,2-Cyclohexanedicarboxylic acidHCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 131729238Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidinium]-5,6-dione trans-2-carboxycyclohexanecarboxylate

Procedure

Compound 15 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, trans-cyclohexane-1,2-dicarboxylic acid and conditions outlined for compound 14. M.p.=208-211° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.90-7.87 (m, 1H), 7.82-7.73 (m, 2H), 7.58-7.53 (m, 1H), 3.06 (s, 2H), 2.96-2.86 (m, 4H), 2.29-2.26 (m, 2H), 1.98-1.91 (m, 4H), 1.77-1.65 (m, 4H), 1.23-1.17 (m, 4H); LCMS: 302 [M+H].

Sources & evidence

ORD record
ord-fefd8e701972431796259d0766b5a200
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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