Water → 16beta-Ethyl-17beta-(N-t-butoxycarbonylleucyl)oxyacetoxy-4-estren-3-one

HRID 64738Notes

Reaction equation

HRID 64738 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].O.[CH2:24]([C@H:26]1[CH2:31][C@H:30]2[C@H:32]3[C@H:41]([CH2:42][CH2:43][C@:28]2([CH3:29])[C@H:27]1[O:45][C:46](=[O:49])[CH2:47]Br)[C@@H:40]1[C:35](=[CH:36][C:37](=[O:44])[CH2:38][CH2:39]1)[CH2:34][CH2:33]3)[CH3:25]>CC(C)=O>[CH2:24]([C@H:26]1[CH2:31][C@H:30]2[C@H:32]3[C@H:41]([CH2:42][CH2:43][C@:28]2([CH3:29])[C@H:27]1[O:45][C:46](=[O:49])[CH2:47][O:15][C:14](=[O:16])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C@@H:40]1[C:35](=[CH:36][C:37](=[O:44])[CH2:38][CH2:39]1)[CH2:34][CH2:33]3)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 7046677316beta-Ethyl-17beta-(N-t-butoxycarbonylleucyl)oxyacetoxy-4-estren-3-oneYield 80.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 40 ml of acetone is dissolved 1.2 g of N-t-butoxycarbonylleucine, and 1.2 g of potassium t-butoxide and 8 ml of water are added, followed by addition of 1.1 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 12 hours. The solvent is then distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure and the residue is subjected to column chromatography. After serial passage of diisopropyl ether-n-hexane mixtures (1:3, 400 ml and 5:2, 750 ml), elution is carried out with 1000 ml of a 4:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.2 g of the above-identified compound as a colorless viscous oil.

Workup

  1. additionare added
  2. temperatureThe mixture is refluxed for 12 hours
  3. distillationThe solvent is then distilled off under reduced pressure
  4. extractionthe residue is extracted with 150 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is distilled off under reduced pressure
  9. washAfter serial passage of diisopropyl ether-n-hexane mixtures (1:3, 400 ml and 5:2, 750 ml), elution
  10. additionis carried out with 1000 ml of a 4:1 mixture of the same solvents
  11. customThe eluate is evaporated under reduced pressure
  12. customto remove the solvent

Sources & evidence

ORD record
ord-372864b4d00b4392ab44102684528265
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

Loading…