Water → HCID 67234805, compound

HRID 1675925Notes

Reaction equation

HRID 1675925 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.O.[CH:14](=[C:21]1[C:37](=[O:38])[C:36]2([CH3:39])[CH:23]([CH:24]3[CH:33]([CH2:34][CH2:35]2)[C:32]2[CH:31]=[CH:30][C:29]([OH:40])=[CH:28][C:27]=2[CH2:26][CH2:25]3)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C.CC(N(C)C)=O>[CH:14](=[C:21]1[C:37](=[O:38])[C:36]2([CH3:39])[CH:23]([CH:24]3[CH:33]([CH2:34][CH2:35]2)[C:32]2[CH:31]=[CH:30][C:29]([O:40][S:1](=[O:4])(=[O:3])[NH2:2])=[CH:28][C:27]=2[CH2:26][CH2:25]3)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 67236326HCID 67236326, compound

Product 1

HCID 67234805HCID 67234805, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

5 ml of a 0.7 M sulphamoyl chloride solution in toluene (3.5 mmol) were concentrated under reduced pressure (30° C. water bath temperature). The residue was cooled to 0° C. (ice bath) and DMA (10 ml) and 16-Benzylidene-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (717 mg, 2.0 mmol, CAB01122) were added. The resulting clear solution was stirred for 1 h at 0° C., then allowed to warm up to room temperature and stirred overnight. Ethyl acetate (50 ml) was added and the solution was washed with water (2×30 ml) and brine. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The resulting off-white solid was dissolved in a small amount of ethyl acetate and precipitated by addition of hexane. Yield: 683 mg (78%) off-white solid. 1H-NMR (CDCl3, 400 MHz), δ: 0.96 (s, 3H), 1.20-2.60 (m, 11H), 2.80-3.02 (m, 3H), 5.38 (s, 2H, —NH2), 7.06 (d, J=2.3 Hz, 1H), 7.11 (dd, J=8.0, 2.3 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.34-7.47 (m, 2H), 7.52-7.65 (m, 2H). LRMS (FAB+): 438.2 (100, [M]+).

Workup

  1. additionwere added
  2. temperatureto warm up to room temperature
  3. stirringstirred overnight
  4. washthe solution was washed with water (2×30 ml) and brine
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe resulting off-white solid was dissolved in a small amount of ethyl acetate
  8. customprecipitated by addition of hexane

Sources & evidence

ORD record
ord-8a3982ca885e485ea5296ff775646cdb
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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