Water → HCID 67352099, compound

HRID 1675926Notes

Reaction equation

HRID 1675926 reaction equation
[BH4-].[Na+].[CH:3](=[C:10]1[C:26](=[O:27])[C:25]2([CH3:28])[CH:12]([CH:13]3[CH:22]([CH2:23][CH2:24]2)[C:21]2[CH:20]=[CH:19][C:18]([O:29][S:30](=[O:33])(=[O:32])[NH2:31])=[CH:17][C:16]=2[CH2:15][CH2:14]3)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C.O>C1COCC1.C(O)C>[CH:3](=[C:10]1[CH:26]([OH:27])[C:25]2([CH3:28])[CH:12]([CH:13]3[CH:22]([CH2:23][CH2:24]2)[C:21]2[CH:20]=[CH:19][C:18]([O:29][S:30](=[O:33])(=[O:32])[NH2:31])=[CH:17][C:16]=2[CH2:15][CH2:14]3)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 67234805HCID 67234805, compound

Product 1

HCID 67352099HCID 67352099, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (100 mg, 2.64 mmol) was added to a solution of sulfamic acid 16-benzylidene-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester (438 mg, 1.0 mmol, CAB01148) in THF (20 ml) and ethanol (20 ml) at 0° C. The mixture was stirred for 1 h at this temperature (TLC-control) and ethyl acetate (100 ml) and water (50 ml) were added. The organic layer was separated and washed with water (50 ml) and brine (50 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and precipitated by addition of diethyl ether. Yield: 440 mg (quant.) white powder. 1H-NMR (CDCl3, 400 MHz), δ: 0.67 (s, 3H), 1.36-1.62 (m, 6H), 2.00-2.10 (m, 2H), 2.22-2.41 (m, 3H), 2.78 (dd, J=17.4, 7.2 Hz, 1H), 2.90-2.96 (m, 2H), 4.15 (d, J=9.4 Hz, 1H, H-17), 4.86 (s, 2H, —NH2), 6.55 (d, J=2.3 Hz, 1H), 7.06 (d, J=2.3 Hz, 1H), 7.10 (dd, J=8.2, 2.3 Hz, 1H), 7.19-7.42 (m, 6H). LRMS (FAB+): 439.2 (100, [M]+).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with water (50 ml) and brine (50 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  7. customprecipitated by addition of diethyl ether

Sources & evidence

ORD record
ord-1c85ad42858b4b89b425e84548c0f920
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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