Methanol → HCID 69520284, compound

HRID 1294658Notes

Reaction equation

HRID 1294658 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CO.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(OCC)(=O)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 444972Fumaric AcidHCID 11245646HCID 11245646, compound

Product 1

HCID 69520284HCID 69520284, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 13A (74 mg, 0.2 mmol) in ethyl acetate:MeOH (5 mL, 10:1) was treated with fumaric acid (Aldrich, 21 mg, 0.2 mmol). The title compound was obtained as solid (90 mg, yield, 95%): 1H NMR (MeOH-d4, 300 MHz) δ 1.75–2.19 (m, 3H), 2.19–2.38 (m, 1H), 2.43–2.56 (m, 1H), 3.20–3.50 (m, 5H), 3.66–3.84 (m, 1H), 4.80 (m, 1H), 6.76 (d, J=8.9 Hz, 2H), 6.90 (d, J=8.9 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 70 (M+H)+. Anal. Calculated for C22H27NO2S.1.0C4H4O4.0.4H2O: C, 63.37; H, 6.50; N, 2.84 63.57; H, 6.20; N, 2.80.

Sources & evidence

ORD record
ord-1de583585f4646ada32ca0d63d1feadc
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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