Sodium Chloride → HCID 86746644, compound

HRID 1613980Notes

Reaction equation

HRID 1613980 reaction equation
[N:1](Cl)=[O:2].[Cl-].[Na+].[N:6]([O:8]S(=O)(=O)O)=O.C1CO[C:15]2([CH2:33][CH2:32][C@@:31]3([CH3:34])[C:17](=[CH:18][CH2:19][C@@H:20]4[C@:30]3([OH:35])[CH2:29][CH2:28][C@@:27]3([CH3:36])[C@H:21]4[CH2:22][CH2:23][C:24]3=[CH:25][CH3:26])[CH2:16]2)O1>C(Cl)Cl>[OH:8][N:6]=[C:15]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C:17]([CH2:18][CH2:19][C@@H:20]3[C@:30]2([OH:35])[CH2:29][CH2:28][C@@:27]2([CH3:36])[C@H:21]3[CH2:22][CH:23]=[C:24]2[C:25](=[N:1][OH:2])[CH3:26])=[CH:16]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 17601Nitrosyl chlorideHCID 82157Nitrosylsulfuric acidHCID 53798444HCID 53798444, compound

Product 1

HCID 86746644HCID 86746644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitrosyl chloride, prepared from sodium chloride and nitrosyl sulfuric acid, was passed into methylene chloride (7 ml) at 0° C., until a burgundy colour had developed. The solution was added in one action to 3,3-ethylenedioxypregna-5,17(20)-dien-9α-ol (301 mg). The reaction mixture was stirred for 3 minutes after which the solvents were evaporated under reduced pressure. The residue was taken up in a mixture of tetrahydrofuran (15 ml) and water (1.5 ml). Triethylamine (1.6 ml) was added dropwise, then the mixture was refluxed for 2 hours. After cooling to room temperature, methylene chloride (100 ml) was added and the mixture was washed twice with a 5% aqueous potassium carbonate solution, dried (MgSO4) and concentrated under reduced pressure. The crude product (251 mg) was chromatographed (silica gel, toluene/acetone 3/1) to afford the title compound as a isomeric mixture of syn and anti 20-oximes, both containing a 3-hydroxyimino group in the syn configuration.

Workup

  1. customwere evaporated under reduced pressure
  2. additionThe residue was taken up in a mixture of tetrahydrofuran (15 ml) and water (1.5 ml)
  3. additionTriethylamine (1.6 ml) was added dropwise
  4. temperaturethe mixture was refluxed for 2 hours
  5. additionmethylene chloride (100 ml) was added
  6. washthe mixture was washed twice with a 5% aqueous potassium carbonate solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product (251 mg) was chromatographed (silica gel, toluene/acetone 3/1)

Sources & evidence

ORD record
ord-9f14e8ec1eeb4051b63ba2aba18620d5
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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