Cesium bicarbonate → HCID 73296155, compound

HRID 1626070Notes

Reaction equation

[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(=O)([O-])O.[Cs+].[CH:15]1([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27]Cl)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[C:4]([O:6][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:21]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:22])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7]

Participants

Reactant 3

HCID 2734983Cesium bicarbonate

HCID 5369209Monomethyl Fumarate

HCID 10376110HCID 10376110, compound

Product 1

HCID 73296155HCID 73296155, compoundYield 50%

Procedure

Following general procedure A, methyl hydrogen fumarate (1.00 g, 7.68 mmol) was reacted with CsHCO3 (2.22 g, 11.52 mmol) and chlorobutyl cyclohexanecarboxylate (2.16 g, 9.98 mmol) at ca. 55° C. to afford 1.2 g (50% yield) of the title compound (44) as a clear oil after purification by mass-guided preparatory. HPLC and lyophilization. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.77 (m, 3H), 3.81 (s, 3H), 2.34-2.28 (m, 1H), 1.91-1.88 (m, 2H), 1.82-1.73 (m, 4H), 1.65-1.62 (m, 2H), 1.47-1.39 (m, 4H), 1.29-1.23 (m, 2H), 0.98-0.94 (t, 3H). MS (ESI): m/z 313.09 (M+H)+.

Sources & evidence

ORD record: ord-c385dbfc67ed4596b210ddf58da4b510
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785443B2

Reaction notes

Loading…