HCID 86733148, compound → HCID 86733140, compound

HRID 267643Notes

Reaction equation

HRID 267643 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][C:15](=[O:23])[CH2:16][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][C:15](=[O:23])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)#[N:2]

Participants

3

Reactant 1

HCID 86733148HCID 86733148, compound

Product 1

HCID 86733140HCID 86733140, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 17β-carbamoyl-5α-androstan-3-one (2.4 g.) and polyphosphate ester (12 g.) in chloroform (125 ml.) was refluxed for 24 hours. After removing the chloroform by evaporation aqueous 10% sodium carbonate (100 ml.) was added, the mixture cooled, and extracted with ether. The ethereal extracts were washed with water, dried (MgSO4), filtered and evaporated to afford a buff solid (2.45 g.). Purification by preparative t.l.c. (ethanol/chloroform 1:19) afforded a solid (1.48 g.) which was further purified by passing through a florisil column and crystallisation from dichloromethane/petrol to give title compound (915 mg.) m.p. 150°-152°; [α]D + 89° (c 1.12%).

Workup

  1. customAfter removing the chloroform
  2. customby evaporation aqueous 10% sodium carbonate (100 ml.)
  3. additionwas added
  4. temperaturethe mixture cooled
  5. extractionextracted with ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto afford a buff solid (2.45 g.)
  11. customPurification by preparative t.l.c
  12. custom(ethanol/chloroform 1:19) afforded a solid (1.48 g.) which
  13. customwas further purified
  14. customby passing through a florisil column and crystallisation from dichloromethane/petrol

Sources & evidence

ORD record
ord-4a1c37e91577429c8371b1c93d00dff8
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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