Hydrochloric Acid → HCID 23336680, compound

HRID 903576Notes

Reaction equation

HRID 903576 reaction equation
[C:1]([C:4]1[C:5]([OH:23])=[C:6]([CH2:20][CH2:21][CH3:22])[C:7]2[S:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:9](=[O:18])[C:8]=2[CH:19]=1)(=[O:3])[CH3:2].[C:24](OCC)(=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26].CCOCC.Cl>CN(C)C=O.O.C(O)C>[O:3]=[C:1]1[C:4]2[CH:19]=[C:8]3[C:9](=[O:18])[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:7]3=[C:6]([CH2:20][CH2:21][CH3:22])[C:5]=2[O:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 23336677HCID 23336677, compound

Product 1

HCID 23336680HCID 23336680, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of step (f) (7.5 g) and diethyl oxalate (24.4 mls) in dry dimethylformamide (200 mls) were added to ether washed 50% sodium hydride (4.3 g) in dry dimethylformamide (250 mls) with stirring under nitrogen. The whole was stirred for a further 24 hours after addition, then poured into ice/water and extracted into ethyl acetate which was dried, filtered and the solvent evaporated to afford a red solid. This was added to ethanol (100 mls) previously saturated with hydrogen chloride gas and refluxed for 15 minutes. The reaction mixture was poured into water, extracted with chloroform, dried and the solvent evaporated to give 4.9 g of the desired product. Structure confirmed by MS and NMR.

Workup

  1. washwashed 50% sodium hydride (4.3 g) in dry dimethylformamide (250 mls)
  2. stirringThe whole was stirred for a further 24 hours
  3. additionafter addition
  4. additionpoured into ice/water
  5. extractionextracted into ethyl acetate which
  6. customwas dried
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customto afford a red solid
  10. temperaturerefluxed for 15 minutes
  11. extractionextracted with chloroform
  12. customdried
  13. customthe solvent evaporated

Sources & evidence

ORD record
ord-305f82a701dc4372b810e4606d44bac0
Source dataset
uspto-grants-1980_10
Patent number
US04228173

Reaction notes

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