HCID 19001597, compound → HCID 19001605, compound

HRID 2259710Notes

Reaction equation

HRID 2259710 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[C:17]1=O)(=[O:5])=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17]1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 19001597HCID 19001597, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19001605HCID 19001605, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of stage (ii) (450 mg) in dry tetrahydrofuran (20 ml) was added cautiously to a stirred suspension of lithium aluminium hydride (200 mg) in dry, freshly distilled tetrahydrofuran (20 ml) at 5°, under nitrogen. The reaction mixture was stirred and heated at reflux for 1 h; cooled to 5°, with stirring, and cautiously treated with a mixture of tetrahydrofuran (6 ml) and water (1 ml). The mixture was filtered through "hyflo". The residue was washed with ethanol. The combined filtrate and washings were evaporated to give a gum which was crystallised from a mixture of ethyl acetate and ether. The product was partitioned between ethyl acetate (30 ml) and 8% sodium bicarbonate (30 ml). The aqueous phase was extracted with ethyl acetate (2×30 ml). The combined organics were dried and evaporated to give a gum, which was crystallised from a mixture of ethyl acetate and cychlohexane to give the title compound (190 mg) as a cream powder, with m.p. 160° -162°.

Workup

  1. customin dry
  2. customat 5°
  3. temperatureheated
  4. temperatureat reflux for 1 h
  5. temperaturecooled to 5°
  6. stirringwith stirring
  7. additioncautiously treated with a mixture of tetrahydrofuran (6 ml) and water (1 ml)
  8. filtrationThe mixture was filtered through "hyflo"
  9. washThe residue was washed with ethanol
  10. customThe combined filtrate and washings were evaporated
  11. customto give a gum which
  12. customwas crystallised from a mixture of ethyl acetate and ether
  13. customThe product was partitioned between ethyl acetate (30 ml) and 8% sodium bicarbonate (30 ml)
  14. extractionThe aqueous phase was extracted with ethyl acetate (2×30 ml)
  15. customThe combined organics were dried
  16. customevaporated
  17. customto give a gum, which
  18. customwas crystallised from a mixture of ethyl acetate and cychlohexane

Sources & evidence

ORD record
ord-82bc4564917f4d03bd2d5329646286c5
Source dataset
uspto-grants-1995_12
Patent number
US05475020

Reaction notes

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