Hydrochloric Acid → HCID 11695645, compound

HRID 1394844Notes

Reaction equation

HRID 1394844 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[N:9]3[CH2:20][C:21]4[C:26]([C:8]=23)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(O)C.[OH-].[Na+]>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]3[CH2:20][C:21]4[C:26]([C:8]=23)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11681730HCID 11681730, compound

Product 1

HCID 11695645HCID 11695645, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of Example 6 in ethanol (8 mL) and 1N NaOH (2.0 mL) was stirred at reflux for 1 hour and cooled to room temperature. The solution was acidified with 1N HCl (2.1 mL) and partially concentrated. The precipitated solid was collected by filtration, washed with water, dissolved in methanol, and filtered. The filtrate was concentrated by boiling to about 0.4 mL, and diluted with diethyl ether. The resulting precipitate was collected by filtration to provide the desired product as a colorless solid. ESI-MS, both positive and negative ion consistent for MW 331, 1H NMR (500 MHz, CD3OD) δ 1.42 (m, 3H), 1.86 (m, 7H), 3.14 (m, J=12.05, 12.05 Hz, 1H), 5.01 (s, 2H), 7.21 (t, J=7.48 Hz, 1H), 7.32 (t, J=7.48 Hz, 1H), 7.44 (d, J=7.63 Hz, 1H), 7.58 (s, 2H), 7.73 (d, J=7.63 Hz, 1H), 7.89 (s, 1H), 7.89 (s, 1H).

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationpartially concentrated
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in methanol
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. additiondiluted with diethyl ether
  9. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7291f74eb55a42dbad2f3d841b4ff430
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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