Methanol → HCID 18779074, compound

HRID 1741451Notes

Reaction equation

HRID 1741451 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14]S(CCCNCCC2C3SC(=O)NC=3C(O)=CC=2)(=O)=O)=[CH:5][CH:4]=1.CO>C1COCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18779045HCID 18779045, compound

Product 1

HCID 18779074HCID 18779074, compoundYield 252.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step b (6 g) was added portion wise to a stirred solution of boranetetrahydrofuran (1.0 M in THF, 85 ml). The reaction was then heated at reflux under an inert atmosphere for 3 hours. The reaction was cooled and methanol (10 mls) was cautiously added. The solvents were removed in vacuo and the residue redissolved in methanol (100 ml) to which was added concentrated hydrochloric acid (sg. 1.18, 4 ml). This solution was heated at reflux for 30 minutes and then the solvent removed in vacuo. The residue was taken up into water and washed with ether. Sodium bicarbonate was added and the aqueous extracted with ethyl acetate. The ethyl acetate was washed with water, brine and dried (MgSO4). The volatiles were removed in vacuo to provide the subtitle compound as a oil (5.5 g) which was used without further purification.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux under an inert atmosphere for 3 hours
  3. temperatureThe reaction was cooled
  4. customThe solvents were removed in vacuo
  5. dissolutionthe residue redissolved in methanol (100 ml) to which
  6. additionwas added concentrated hydrochloric acid (sg. 1.18, 4 ml)
  7. temperatureThis solution was heated
  8. temperatureat reflux for 30 minutes
  9. customthe solvent removed in vacuo
  10. washwashed with ether
  11. additionSodium bicarbonate was added
  12. extractionthe aqueous extracted with ethyl acetate
  13. washThe ethyl acetate was washed with water, brine
  14. dry with materialdried (MgSO4)
  15. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-385cceb4f9fe48ed9168f8206d69797f
Source dataset
uspto-grants-1999_10
Patent number
US05973167

Reaction notes

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