Chlorosulfamic acid → HCID 12020528, compound

HRID 843290Notes

Reaction equation

HRID 843290 reaction equation
[H-].[Na+].[CH2:3]([NH:7][C:8]([C:10]1[C@:11]2([CH2:27][CH2:26][C@H:25]3[C@@H:16]([CH2:17][CH2:18][C:19]4[CH:20]=[C:21]([OH:28])[CH:22]=[CH:23][C:24]=43)[C@@H:13]2[CH2:14][CH:15]=1)[CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6].Cl[S:30]([NH2:33])(=[O:32])=[O:31].C(=O)(O)[O-].[Na+]>CN(C=O)C>[S:30](=[O:32])(=[O:31])([O:28][C:21]1[CH:22]=[CH:23][C:24]2[C@@H:25]3[C@H:16]([C@H:13]4[C@@:11]([CH2:27][CH2:26]3)([CH3:12])[C:10]([C:8](=[O:9])[NH:7][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:15][CH2:14]4)[CH2:17][CH2:18][C:19]=2[CH:20]=1)[NH2:33]

Participants

6

Reactant 4

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 12019734HCID 12019734, compound

Product 1

HCID 12020528HCID 12020528, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (20 mg) was added to a solution comprising 73 mg of compound 10a in 2 ml of anhydrous DMF at 0° C. The solution was stirred for 25 minutes and 126 mg of chlorosulfonamide was added in one portion. The solution was then stirred at room temperature for 2 hours. Ice and saturated sodium bicarbonate solution was added to the reaction mixture. The precipitate formed was filtered and washed with water. The residue was purified by chromatography on silica gel (CHCl3:methanol, 50:1), yielding compound 11a (85 mg, 96%). FAB-MS m/z 433 (M+H)+; 1H NMR (270 MHz, DMSO-d6) δ 0.88 (t, 3H, J=7.5 Hz, CH2CH3), 0.91 (s, 3H, CH3), 3.08 (dt, 2H, J=5.6, 6.6 Hz, NHCH2), 6.34 (s, 1H, 16-CH), 6.97 (s, 1H, ArH), 7.01 (dd, 1H, J=2.6, 8.6 Hz, ArH), 7.33 (d, 1H, J=8.6 Hz, ArH), 7.71 (t, 1H, J=5.6 Hz, NHCH2), 7.88 (s, 2H, NH2).

Workup

  1. customat 0° C
  2. stirringThe solution was then stirred at room temperature for 2 hours
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe residue was purified by chromatography on silica gel (CHCl3:methanol, 50:1)

Sources & evidence

ORD record
ord-f137591f6fb9442b9ab038a997319c88
Source dataset
uspto-grants-2002_04
Patent number
US06376687B1

Reaction notes

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