HCID 86733150, compound → HCID 86733149, compound

HRID 267644Notes

Reaction equation

HRID 267644 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH:15]=[CH:16][CH2:17]1)[CH2:12][CH2:11]3)(=O)[NH2:2]>C(Cl)(Cl)Cl>[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH:15]=[CH:16][CH2:17]1)[CH2:12][CH2:11]3)#[N:2]

Participants

3

Reactant 1

HCID 86733150HCID 86733150, compound

Product 1

HCID 86733149HCID 86733149, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 17β-carbamoyl-5α-androst-2-ene (4.33 g.,) and polyphosphate ester (25.0 g.) in chloroform (250 ml.) was refluxed for 16 hours. The residue, after removal of the chloroform, was neutralised by the careful addition of aqueous 10% sodium carbonate (150 ml.) with cooling and extracted with ether. The etheral solution was washed with water, dried (MgSO4) filtered and evaporated to a partly crystalline residue which, after washing with a small portion of ice-cold ether, afforded a crystalline product (3.34 g.). The etheral washings were chromatographed on a column (1 inch × 6 inches) of florisil. Elution with petrol (200 ml.) afforded further product (660 mg.) gaining a total yield of 4.00 g. A sample (300 mg.) was recrystallised from petrol to afford title compound (260 mg.); m.p. 110°-112°: [α]D + 108°, (c 0.6).

Workup

  1. customThe residue, after removal of the chloroform
  2. additionwas neutralised by the careful addition of aqueous 10% sodium carbonate (150 ml.)
  3. temperaturewith cooling
  4. extractionextracted with ether
  5. washThe etheral solution was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to a partly crystalline residue which
  9. washafter washing with a small portion of ice-cold ether
  10. customafforded a crystalline product (3.34 g.)
  11. customThe etheral washings were chromatographed on a column (1 inch × 6 inches) of florisil
  12. washElution with petrol (200 ml.)
  13. customafforded further product (660 mg.)
  14. customA sample (300 mg.) was recrystallised from petrol

Sources & evidence

ORD record
ord-09872acb672e4f9b9d8875657d5b2cfe
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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