Hydrochloric Acid → HCID 136397072, compound

HRID 2110611Notes

Reaction equation

HRID 2110611 reaction equation
[NH2:1][C@@:2]1([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([NH:23]C(=O)OC(C)(C)C)=[CH:22][C:16]=3[S:15](=[O:32])(=[O:31])[N:14]=2)[C:3]1=[O:33].[C:39](=[O:42])([O-])[O-].[K+].[K+].[CH3:45][O:46][C:47]1[CH:48]=[C:49]([S:55](Cl)(=[O:57])=[O:56])[CH:50]=[C:51](OC)[CH:52]=1.Cl.N1C=CC=CC=1.[CH3:66][S:67](Cl)(=[O:69])=[O:68]>CN(C)C=O>[OH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C@@:2]([NH:1][S:55]([C:49]2[CH:48]=[C:47]([O:46][CH3:45])[CH:52]=[CH:51][C:50]=2[O:42][CH3:39])(=[O:57])=[O:56])([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:3](=[O:33])[C:4]=1[C:13]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([NH:23][S:67]([CH3:66])(=[O:69])=[O:68])=[CH:22][C:16]=2[S:15](=[O:31])(=[O:32])[N:14]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 15567167HCID 15567167, compoundHCID 136396995HCID 136396995, compound

Product 1

HCID 136397072HCID 136397072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 83B (138 mg, 0.26 mmol) in N,N-dimethylformamide (1 mL) was added potassium carbonate (70 mg, 0.51 mmol) and 3,5-dimethoxybenzenesulfonyl chloride (61 mg, 0.26 mmol) and the solution was stirred at room temperature for 16 hours. The solution was poured into 1N HCl (5 mL) and extracted with ethyl acetate (3×5 mL), the combined organic extracts washed with brine (1×5 mL) and solvent removed in vacuo to yield crude product which was purified by column chromatography on silica gel (2-4% methanol/chloroform). The pure product was dissolved in 4M HCl in dioxane (2 mL) and stirred at room temperature for 3 hours, solvent removed in vacuo and the crude residue dissolved in dichloromethane (1 mL) and pyridine (68 μL, 0.84 mmol) and methanesulfonyl chloride (26 uL, 0.36 mmol) added and the solution stirred at room temperature for 16 hours. Solvent was removed in vacuo and the crude residue was purified by column chromatography on silica gel (2-4% methanol/chloroform) to give the title compound as a colorless solid; 1H NMR (d6-dmso) δ 13.69(s, 1H), 10.23 (s, 1H), 8.49 (s, 1H), 8.02, 7.99 (d, 1H), 7.65-7.55 (q, 3H), 7.40-7.30 (t, 1H), 7.25-7.15 (q, 2H), 7.06, 7.03 (d, 1H), 6.90, 6.89, 6.88, 6.86 (dd, 1H), 6.36, 6.34 (d, 1H), 3.95 (s, 3H), 3.41 (s, 3H), 3.08 (s, 3H), 2.31-2.18 (m, 1H), 1.96-1.84 (m, 1H), 1.29-1.17 (m, 1H), 0.83-0.69 (m, 1H), 0.69-0.57 (q, 6H), 0.36-0.23 (m, 1H); MS (ESI) m/z 719 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washthe combined organic extracts washed with brine (1×5 mL) and solvent
  3. customremoved in vacuo
  4. customto yield crude product which
  5. customwas purified by column chromatography on silica gel (2-4% methanol/chloroform)
  6. dissolutionThe pure product was dissolved in 4M HCl in dioxane (2 mL)
  7. stirringstirred at room temperature for 3 hours
  8. customsolvent removed in vacuo
  9. dissolutionthe crude residue dissolved in dichloromethane (1 mL)
  10. stirringthe solution stirred at room temperature for 16 hours
  11. customSolvent was removed in vacuo
  12. customthe crude residue was purified by column chromatography on silica gel (2-4% methanol/chloroform)

Sources & evidence

ORD record
ord-9b8fb1c1b42744e186d44f86c8980ff2
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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