HCID 10314079, compound → HCID 136351968, compound
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].CS[C:18](SC)=[C:19]1[C:28](=[O:29])[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:20]1=[O:34]>C1(C)C=CC=CC=1>[CH2:30]([N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][N:23]=2)[C:28]([OH:29])=[C:19]([C:18]2[NH:1][C:2]3[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=3[S:7](=[O:8])(=[O:9])[N:10]=2)[C:20]1=[O:34])[CH2:31][CH2:32][CH3:33]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The product of Example 309G (110 mg, 0.43 mmol) and the product of Example 315B (140.6 mg, 0.43 mmol) were reacted in toluene (5 mL) at 100° C. for 3 hours. The reaction was concentrated under reduced pressure and the residue was purified by chromatography on silica gel using a Biotage-12 m column eluting with 1:99 methanol:dichloromethane to give the title compound as a white solid (114 mg, 54.6%). The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz,CDCCl3) δ ppm 1.00 (t, J=7.35 Hz, 3 H), 1.46 (m, 2 H), 1.74 (m, 2 H), 3.45 (s, 3 H), 4.56 (m, 2 H), 4.80 (s, 2 H), 4.84 (s, 2 H), 7.09 (s, 1 H), 7.26 (s, 1 H), 7.36 (dd, J=8.09, 4.41 Hz, 1 H), 8.57 (dd, J=8.09, 1.84 Hz, 1 H), 8.81 (dd, J=4.78, 1.84 Hz, 1 H), 15.06 (s, 1 H), 15.11 (s, 1 H).
Workup
- concentrationThe reaction was concentrated under reduced pressure
- customthe residue was purified by chromatography on silica gel using a Biotage-12 m column
- washeluting with 1:99 methanol
Sources & evidence
- ORD record
- ord-4464ead5c7954194a94e10f6ebb47d29
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902203B2
Reaction notes
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