Fumaric Acid → HCID 69431496, compound

HRID 969972Notes

Reaction equation

HRID 969972 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH2:23])[CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]>C(OCC)(=O)C.C(O)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH2:23])[CH:17]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11483659HCID 11483659, compound

Product 1

HCID 69431496HCID 69431496, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 4A in ethyl acetate/ethanol (v.1:1, 4 mL) was treated with fumaric acid (40 mg, 0.34 mmol) at ambient temperature for 15 hours. The title compound was obtained as a solid (115 mg, yield, 77%). 1H NMR (MeOH-d4, 300 MHz) δ 1.79-2.16 (m, 3H), 2.18 (s, 3H), 2.24-2.39 (m, 1H), 2.46-2.54 (m, 1H), 3.20-3.42 (m, 5H), 3.71-3.81 (m, 1H), 6.68 (s, 2H), 6.83 (dd, J=7.8, 1.7 Hz, 1H), 6.94 (d, J=1.7 Hz, 1H), 6.97-7.06 (m, 3H), 7.51 (dt, J=8.5, 2.1 Hz, 2H) ppm. MS (Cl/NH3): m/z 309 (M+H)+. Anal. Calculated for C20H24N2O.C4H4O4: C, 67.91; H, 6.65; N, 6.60. Found: C, 67.62; H, 6.45; N, 6.43.

Sources & evidence

ORD record
ord-ba590e2a88f54cc3a335b3e10143bc0e
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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