Sodium Iodide → HCID 12804708, compound

HRID 223435Notes

Reaction equation

HRID 223435 reaction equation
C1[O:30][C:4]([C@@H:6]2[C@:23]3([CH3:24])[C@H:9]([C@H:10]4[C@H:20]([C@H:21]([NH2:25])[CH2:22]3)[C@:18]3([CH3:19])[C@H:13]([CH2:14][C@H:15]([OH:29])[C@@H:16]([O:26][CH2:27][CH3:28])[CH2:17]3)[CH2:12][CH2:11]4)[CH2:8][CH2:7]2)([CH3:5])OC1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Br[CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43]>C(O)C>[CH2:27]([O:26][C@H:16]1[CH2:17][C@@:18]2([CH3:19])[C@@H:13]([CH2:12][CH2:11][C@@H:10]3[C@@H:20]2[C@H:21]([NH:25][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:22][C@@:23]2([CH3:24])[C@H:9]3[CH2:8][CH2:7][C@@H:6]2[C:4](=[O:30])[CH3:5])[CH2:14][C@@H:15]1[OH:29])[CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 22821801HCID 22821801, compound

Product 1

HCID 12804708HCID 12804708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11α-amino-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one 20-ethylene acetal (20 g) in ethanol (200 ml) was stirred with K2CO3 (25 g), NaI (1 g) and 1-bromo-3-methylbutane (50 ml) and the mixture was heated at reflux for 24 h. The excess K2CO3 was removed by filtration and washed with ethanol. The filtrate and washings were acidified with 2M-HCl to pH 2, washed with ether and the ether wash in turn washed with M-HCl and water (x3). The aqueous layers were brought to pH 10 with 2M-NaOH and the resulting suspension was extracted with ether (x2). The ether layers were combined, washed with water (x2), dried and evaporated to leave a froth (18.96 g), which was purified by column chromatography eluted with CHCl3 /MeOH (19:1) and crystallised from acetonitrile to give the title compound (9.211 g), m.p. 110.5°-112° C., [α ]D +56°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe excess K2CO3 was removed by filtration
  4. washwashed with ethanol
  5. washwashed with ether
  6. washthe ether wash in turn
  7. washwashed with M-HCl and water (x3)
  8. extractionthe resulting suspension was extracted with ether (x2)
  9. washwashed with water (x2)
  10. customdried
  11. customevaporated
  12. customto leave a froth (18.96 g), which
  13. customwas purified by column chromatography
  14. washeluted with CHCl3 /MeOH (19:1)
  15. customcrystallised from acetonitrile

Sources & evidence

ORD record
ord-4c4fd71dc9224d8db987262f8e85e743
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

Loading…