Sodium Bicarbonate → HCID 69105088, compound

HRID 2224043Notes

Reaction equation

HRID 2224043 reaction equation
[C:1]([C@@:3]12[CH2:20][CH2:19][C:18]3[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:13]=3[C@H:12]1[C:11](=[O:23])[CH2:10][C@@:8]1([CH3:9])[C@H:4]2[CH2:5][CH2:6][C@@H:7]1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)#[N:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([C@@:3]12[CH2:20][CH2:19][C:18]3[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:13]=3[C@H:12]1[CH:11]([OH:23])[CH2:10][C@@:8]1([CH3:9])[C@H:4]2[CH2:5][CH2:6][C@@H:7]1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)#[N:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69104800HCID 69104800, compound

Product 1

HCID 69105088HCID 69105088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 33.1 g of steroid 3 in 400 ml of THF was cooled to 0° C., mixed in portions with 51.0 g of LTBAH, and the solution was stirred for 1 hour while cooling was continued and for 1 hour at room temperature. 25 ml of saturated sodium bicarbonate solution was added in drops to the reaction solution at 0° C., the precipitate that was produced was separated by filtration on Celite, and the filtrate was concentrated by evaporation to a very large extent. The residue was extracted several times with ethyl acetate, the collected organic phases were then washed with brine, dried on magnesium sulfate, and the solvent was removed in a vacuum. In this way, 27.6 g (97%) of foamy 4 was obtained, which was used without further purification in the next stage.

Workup

  1. additionmixed in portions with 51.0 g of LTBAH
  2. temperaturewhile cooling
  3. waitwas continued and for 1 hour at room temperature
  4. customthe precipitate that was produced
  5. customwas separated by filtration on Celite
  6. concentrationthe filtrate was concentrated by evaporation to a very large extent
  7. extractionThe residue was extracted several times with ethyl acetate
  8. washthe collected organic phases were then washed with brine
  9. customdried on magnesium sulfate
  10. customthe solvent was removed in a vacuum
  11. customIn this way, 27.6 g (97%) of foamy 4 was obtained
  12. customwhich was used without further purification in the next stage

Sources & evidence

ORD record
ord-08d16a3c091d4289b1269f8923affff8
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

Loading…