Hydrochloric Acid → HCID 10219783, compound

HRID 650114Notes

Reaction equation

HRID 650114 reaction equation
[C:1]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13]C(=O)C)([CH3:4])([CH3:3])[CH3:2].O.Cl>C1COCC1>[C:1]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 1279601HCID 1279601, compound

Product 1

HCID 10219783HCID 10219783, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Step A (2.35 g, 0.010 mol) was dissolved in THF wand 10 mL of water was added to form a clear suspension. Hydrochloric acid (5%) was added until the solution reached a pH˜1. The reaction mixture was then refluxed for 24 hours. TLC indicated that about half of the starting material remained, so an additonal 10 mL of 5% hydrochloric acid was added and the reaction mixture was refluxed for 24 hours. The THF was then removed by rotoevaporation and the remaining aqueous mixture was extracted with hexanes (2×20 mL). The combined hexane layers were washed with water (2×40 mL), dried over MgSO4 and the hexane removed in vacuo to provide 1.56 g (80.8% yield) of the title compound as a white crystalline solid, m.p. 78-79.5° C.

Workup

  1. additionwas added
  2. customto form a clear suspension
  3. temperatureThe reaction mixture was then refluxed for 24 hours
  4. additionwas added
  5. temperaturethe reaction mixture was refluxed for 24 hours
  6. customThe THF was then removed by rotoevaporation
  7. extractionthe remaining aqueous mixture was extracted with hexanes (2×20 mL)
  8. washThe combined hexane layers were washed with water (2×40 mL)
  9. dry with materialdried over MgSO4
  10. customthe hexane removed in vacuo

Sources & evidence

ORD record
ord-0693be00f88a48e58e7d7636c98dab9e
Source dataset
uspto-grants-2001_08
Patent number
US06271265B1

Reaction notes

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