Methanol → HCID 69518845, compound

HRID 1294656Notes

Reaction equation

HRID 1294656 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]([S:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:12][CH:11]=1)[CH2:2]2.CO.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(OCC)(=O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([S:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 887MethanolHCID 444972Fumaric AcidHCID 11738931HCID 11738931, compound

Product 1

HCID 69518845HCID 69518845, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 11A (38 mg, 0.12 mmol) in ethyl acetate:MeOH (5 mL, 10:1) was treated with fumaric acid 17.4 mg (0.15 mmol) at room temperature overnight. The title compound was obtained as a solid (30 mg, yield, 66%). 1H NMR (MeOH-d4, 300 MHz) δ 1.75–2.19 (m, 3H), 2.19–2.38 (m, 1H), 2.33–2.46 (m, 1 3.03–3.27 (m, 5H), 3.50–3.64 (m, 1H), 4.70 (m, 1H), 6.67 (s, 1H), 6.76 (d, J=8.9 Hz, 2H), 6.87 (d, J=8.9 Hz, 2H), 7.15–7.26 (m, 4H) ppm. MS (DCl/NH3) m/z 328 (M+H)+. Anal. Calculated for C19H21NO2S.0.5C4H4O4.0.4H2O C, 64.23; H 6.11; N, 3.57. Found: C, 64.14; H, 5.83; N, 3.49.

Sources & evidence

ORD record
ord-b2b7f10be1cb497fba429927f367048e
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

Loading…