Chlorosulfamic acid → HCID 59850961, compound

HRID 1034929Notes

Reaction equation

HRID 1034929 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:28]=[CH:27][C:7]2[S:8][CH:9]=[C:10]([CH:11]([CH2:25][OH:26])[C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[O:13])[C:6]=2[CH:5]=1.[S:29](Cl)(=[O:32])(=[O:31])[NH2:30]>CN(C=O)C>[Cl:3][C:4]1[CH:28]=[CH:27][C:7]2[S:8][CH:9]=[C:10]([CH:11]([C:12](=[O:13])[NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)[CH2:25][O:26][S:29](=[O:32])(=[O:31])[NH2:30])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acid2×HCID 24758Sodium hydrideHCID 59850926HCID 59850926, compound

Product 1

HCID 59850961HCID 59850961, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 95% NaH (0.017 g, 0.68 mmol) in DMF (2 mL) at 0° C. was added a solution of Compound 136 (0.10 g, 0.26 mmol) in DMF (2 mL) dropwise. The suspension was stirred at 0° C. for 1 h, then sulfamoyl chloride (0.067 g, 0.58 mmol) was added as a solid. After stirring for 1 h at 0° C., the mixture was treated with excess sulfamoyl chloride. After stirring overnight, the reaction was quenched with water and extracted with EtOAc (3×5 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure at rt. The residue was purified by flash column chromatography (silica, 0-40% EtOAc/hexanes) to yield Compound 120 (0.10 g) as a white foam: HPLC: 4.12 min; MS (ES) m/z 461 (MH+); 1H NMR (DMSO-d6) δ 4.29-4.34 (m, 1H), 4.65-4.75 (m, 2H), 7.39-7.50 (m, 3H), 7.57-7.64 (m, 1H), 7.81-7.90 (m, 4H), 8.09 (d, 1H, J=8.5 Hz), 8.215 (d, 1H, J=2 Hz), 8.34 (s, 1H), 10.55 (s, 1H).

Workup

  1. stirringAfter stirring for 1 h at 0° C.
  2. stirringAfter stirring overnight
  3. customthe reaction was quenched with water
  4. extractionextracted with EtOAc (3×5 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure at rt
  9. customThe residue was purified by flash column chromatography (silica, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6ea330ed85374468918af677bf209093
Source dataset
uspto-grants-2013_10
Patent number
US08546358B2

Reaction notes

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