Hydrochloric Acid → HCID 136347194, compound

HRID 601319Notes

Reaction equation

HRID 601319 reaction equation
[CH:1]1([NH:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:18]=4[S:17](=[O:27])(=[O:26])[N:16]=3)=[C:11]([OH:28])[C:10]3[S:29][CH:30]=[CH:31][C:9]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][C:40]([NH2:42])=[O:41].Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O>[CH:1]1([NH:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([O:25][CH2:39][C:40]([NH2:42])=[O:41])=[CH:24][C:18]=4[S:17](=[O:27])(=[O:26])[N:16]=3)=[C:11]([OH:28])[C:10]3[S:29][CH:30]=[CH:31][C:9]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 136374263HCID 136374263, compound

Product 1

HCID 136347194HCID 136347194, compoundYield 21.5%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example 324E (0.209 g, 0.45 mmol) was reacted with cesium carbonate (0.589 g, 1.81 mmol), 2-bromoacetamide (0.125 g, 0.91 mmol) and a catalytic amount of tetrabutylammonium iodide in N,N-dimethylformamide (8 mL) at 25° C. for 18 hours. The reaction was diluted with 50 mL water, acidified to pH 2 with 1 M hydrochloric acid. The resulting precipitate was collected by filtration and purified by column chromatography on silica gel eluting with 5% methanol in chloroform to give the title compound (0.050 g, 21% yield). The sodium salt of the title compound was prepared according to the procedure of Example 1D. MS (ESI−) m/z 516 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.48 (m, 10 H) 4.59 (s, 2 H) 6.50 (s, 1 H) 7.39 (m, 2 H) 7.44 (s, 1 H) 7.48 (d, J=5.15 Hz, 1 H) 7.65 (s, 1 H) 7.70 (d, J=9.56 Hz, 1 H) 8.28 (d, J=5.15 Hz, 1 H) 14.13 (s, 1 H) 14.89 (s, 1 H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. custompurified by column chromatography on silica gel eluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-35dda5f23fc140a694391c20c003324e
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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