Hydrochloric Acid → HCID 68976129, compound

HRID 1867948Notes

Reaction equation

HRID 1867948 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C(=O)C)=[CH:18][CH:17]=1)[O:14][CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CCO>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C@@H:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[O:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57980886HCID 57980886, compound

Product 1

HCID 68976129HCID 68976129, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of 6c (132 mg, 0.35 mmol) in EtOH (5 mL) 0.469 g of a freshly prepared solution of potassium hydroxide (253.2 mg in 5.013 g H2O, 0.045M, 1.1eq.) was added. The mixture was stirred at 23-25° C. for 1 h (completion monitored by TLC) and neutralized with 0.1% HCl (neutral by pH indicator paper). Solvent was evaporated in vacuo and the residue dissolved in ethyl acetate and flash filtered through a pad of silica gel to remove inorganic impurities. The silica gel was washed with ethyl acetate, fractions combined and solvent evaporated in vacuo to afford 107 mg (92%) of 6e.

Workup

  1. customSolvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. filtrationflash filtered through a pad of silica gel
  4. customto remove inorganic impurities
  5. washThe silica gel was washed with ethyl acetate, fractions
  6. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-61f0c37705e04dc1a8c52c64ffb95668
Source dataset
uspto-grants-2009_12
Patent number
US07632972B2

Reaction notes

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