Hydrochloric Acid → HCID 13891056, compound

HRID 1722666Notes

Reaction equation

HRID 1722666 reaction equation
[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11][CH:12]=[O:13])[O:8][C:7](=[O:14])[NH:6]1)[CH:2]([CH3:4])[CH3:3].[CH2:15]([Mg]Br)[CH2:16][CH:17]([CH3:19])[CH3:18].Cl>C1COCC1.CC(C)=O>[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11][C:12](=[O:13])[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[O:8][C:7](=[O:14])[NH:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13891054HCID 13891054, compoundHCID 178418529HCID 178418529, compound

Product 1

HCID 13891056HCID 13891056, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 g (0.01 mole) portion of the compound from Example 26 was dissolved in THF (50 mL) and treated at 0°-5° C. with 37.5 mL of an 0.8 M solution of isopentyl magnesium bromide in THF. The reaction was stirred for 2 hours at room temperature and then poured into ice water which contained 6.5 mL of 6 N HCl. The mixture was extracted with methylene chloride. Evaporation of the dried methylene chloride solution gave a quantitative yield of the Grignard adduct. This material was dissolved in 300 mL of acetone and treated by dropwise addition with Jones solution until the orange color persisted. The chromium salts were filtered and the filtrate was evaporated. The residue was diluted with ether and the resulting solution was washed successively with aqueous NaHCO3 and brine solution. After drying over MgSO4, the solvent was evaporated to give 1.7 g (66%) of product as an oil. NMR (300 MHz, CDCl3, ppm): 0.86-0.96 (m, 12H), 2.41 (M, 2H), 2.67 (m, 2H), 3.5 (m, 1H), 4.15 (m, 1H).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. customEvaporation of the dried methylene chloride solution
  3. customgave a quantitative yield of the Grignard adduct
  4. additiontreated by dropwise addition with Jones solution until the orange color
  5. filtrationThe chromium salts were filtered
  6. customthe filtrate was evaporated
  7. additionThe residue was diluted with ether
  8. washthe resulting solution was washed successively with aqueous NaHCO3 and brine solution
  9. dry with materialAfter drying over MgSO4
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b4bb661f5ad14d5786ee78a6de9bb134
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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