Hydrochloric Acid → HCID 86754947, compound

HRID 611515Notes

Reaction equation

HRID 611515 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23]C(=O)C2C=CC=CC=2)=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][N:40]1[C:44]([CH3:46])([CH3:45])[C:43]2[CH:47]=[CH:48][CH:49]=[C:50]([N+:51]([O-:53])=[O:52])[C:42]=2[Se:41]1)(=O)C.[OH-].[Na+].Cl>C1COCC1.CO>[OH:23][C:16]1[CH:17]=[CH:18][C:19]2[C@@H:20]3[C@H:11]([C@H:8]4[C@@:6]([CH2:22][CH2:21]3)([CH3:7])[C@@H:5]([OH:4])[CH2:10][CH2:9]4)[C@H:12]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][N:40]3[C:44]([CH3:45])([CH3:46])[C:43]4[CH:47]=[CH:48][CH:49]=[C:50]([N+:51]([O-:53])=[O:52])[C:42]=4[Se:41]3)[CH2:13][C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86754948HCID 86754948, compound

Product 1

HCID 86754947HCID 86754947, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-{8-[17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl]octyl}-3,3-dimethyl-7-nitrobenzisoselenazoline (115 mg, 0.15 mmol) is dissolved in 2 ml of THF and 1 ml of methanol. To the obtained mixture is then added an aqueous solution of NaOH (1 ml, 1N, 1.0 mmol). The reaction medium is stirred at room temperature for 22 hours, then neutralized with an aqueous solution of HCl (1N). The mixture is extracted with ethyl acetate. The combined organic phases are washed with a saturated aqueous solution of NaCl, dried over MgSO4 and evaporated. The residue is purified by silica gel column chromatography (eluent: EtOAc:cyclohexane, 1:3) to provide the expected product (95 mg, 94%) as a deep red solid.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washThe combined organic phases are washed with a saturated aqueous solution of NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue is purified by silica gel column chromatography (eluent: EtOAc:cyclohexane, 1:3)

Sources & evidence

ORD record
ord-1abd715a5d2a4846815156a22c407008
Source dataset
uspto-grants-1999_12
Patent number
US06001825

Reaction notes

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