Hydrochloric Acid → HCID 135885173, compound

HRID 2110592Notes

Reaction equation

HRID 2110592 reaction equation
[C:1]([N:4]([O:42][CH3:43])[C:5]1([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26]C(=O)OC(C)(C)C)=[CH:25][C:19]=3[S:18](=[O:35])(=[O:34])[N:17]=2)[C:6]1=[O:36])(=[O:3])[CH3:2].Cl.C(N(CC)CC)C.[CH3:52][S:53](Cl)(=[O:55])=[O:54]>O1CCOCC1>[OH:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([N:4]([O:42][CH3:43])[C:1](=[O:3])[CH3:2])([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:6](=[O:36])[C:7]=1[C:16]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([NH:26][S:53]([CH3:52])(=[O:55])=[O:54])=[CH:25][C:19]=2[S:18](=[O:34])(=[O:35])[N:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136383507HCID 136383507, compound

Product 1

HCID 135885173HCID 135885173, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of Example 39A (16 mg, 0.026 mmol) and 4 N HCl in dioxane (0.26 mL) was stirred at room temperature for 4 h and then concentrated in vacuo. The resulting residue was taken up in dichloromethane (1 mL) and triethylamine (36 μL, 0.3 mmol) and methanesulfonyl chloride (10μL, 0.13 mmol) were then added. The reaction solution was stirred at room temperature for 2 h. The solution was then washed with aqueous 1 N HCl (2×0.5 mL), dried (Na2SO4), and concentrated in vacuo. The residue was then dissolved in methanol (1 mL) and treated with excess of K2CO3 for 30 min. The mixture was diluted with ethyl acetate (3 mL) and filtered. The filtrate was washed with aqueous 1 N HCl (2×1 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (1%→3%→5% methanol/dichloromethane) afforded the title compound as a yellow solid (8 mg, 53%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.38-0.56 (m, 1H), 0.60-0.73 (m, 6H), 0.91-1.09 (m, 1H), 1.17-1.39 (m, 2H), 2.01 (s, 3H), 2.11-2.32 (m, 1H), 3.03 (s, 3H), 4.05 (s, 3H), 7.32-7.62 (m, 7H), 8.05 (d, J=7.72 Hz, 1H), 10.05 (s, 1H), 14.46 (s, 1H); MS m/z 591.1 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe reaction solution was stirred at room temperature for 2 h
  3. washThe solution was then washed with aqueous 1 N HCl (2×0.5 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was then dissolved in methanol (1 mL)
  7. additiontreated with excess of K2CO3 for 30 min
  8. additionThe mixture was diluted with ethyl acetate (3 mL)
  9. filtrationfiltered
  10. washThe filtrate was washed with aqueous 1 N HCl (2×1 mL)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65fb9a5ecac74307b459830b474da816
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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