Hydrochloric Acid → HCID 54464593, compound

HRID 365701Notes

Reaction equation

HRID 365701 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][N:20]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=[C:15]([CH2:33][N:34]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:14]=2)C(=O)C2=CC=CC=C12.[OH-].[Na+].Cl.S(Cl)(Cl)=O>O1CCOCC1.C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH2:33][N:34]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[N:16]=[C:17]([CH2:19][N:20]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 53853795HCID 53853795, compound

Product 1

HCID 54464593HCID 54464593, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound (23) (400 mg, 0.55 mmol) was dissolved in dioxane (5 ml) and sodium hydroxide (2 M, 5 ml) was added. A mixture was stirred neutralized with conc. hydrochloric acid and evaporated almost to dryness. The residue was treated with hydrazine hydrate (2.0 ml) dissolved in ethanol (10 ml) and refluxed for 6 h. Volatile matter was evaporated and coevaporated with dry acetonitrile. The residue obtained was suspended in dry ethanol (50 ml) previously treated with thionyl chloride (4 ml). The mixture was refluxed for 2 h, filtered, evaporated and partitioned between saturated sodium hydrogen carbonate and chloroform. Combined chloroform extracts were dried over sodium sulphate, concentrated and finally purified using short column chromatography.

Workup

  1. customevaporated almost to dryness
  2. additionThe residue was treated with hydrazine hydrate (2.0 ml)
  3. dissolutiondissolved in ethanol (10 ml)
  4. temperaturerefluxed for 6 h
  5. customVolatile matter was evaporated
  6. customThe residue obtained
  7. temperatureThe mixture was refluxed for 2 h
  8. filtrationfiltered
  9. customevaporated
  10. custompartitioned between saturated sodium hydrogen carbonate and chloroform
  11. dry with materialCombined chloroform extracts were dried over sodium sulphate
  12. concentrationconcentrated
  13. customfinally purified

Sources & evidence

ORD record
ord-384ccc08aab44a1b8e4ac19b6498eba6
Source dataset
uspto-grants-2000_10
Patent number
US06127529

Reaction notes

Loading…