Hydrochloric Acid → HCID 15702749, compound

HRID 867452Notes

Reaction equation

HRID 867452 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:6]1[CH:19]([CH2:24][C:25]([O:27]CC)=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][C:5]2=1.[Li+].[OH-].C(OCC)(=O)C.Cl>C(O)C.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:6]1[CH:19]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][C:5]2=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 15702748HCID 15702748, compound

Product 1

HCID 15702749HCID 15702749, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

To 230 mg of the ester from Step 1 in 3.0 mL of ethanol was added 2.2 mL of 0.5M aqueous LiOH and the resultant mixture heated at reflux for 8 h. The reaction mixture was then cooled to room temperature, poured into ethyl acetate and acidified with concentrated HCl. The organic layer was separated, washed with 1N HCl and brine (2x) and dried over MgSO4. Concentration gave a yellow oil which solidified on standing. Trituration with hexane gave the title compound. IR (KBr) 1710 cm-1. 'H NMR (CDCl3, 250 MHz) w 1.35-1.70 (m, 2H), 1.80-2.12 (m, 4H), 2.50-2.65 (m, H), 2.54 (d,d, J=6.5, 16.0 Hz, 1H), 2.72 (d,d, J=8.5 Hz, 1H), 2.95-3.06 (m, 1H), 3.46-3.58 (m, 1H), 5.28 (d, J=7.5 Hz, 1H), 5.43 (d, J=7.5 Hz, 1H), 6.80-6.92 (m, 1H), 6.83 (d, J=8.0 Hz, 2H), 7.26 (d,d, J=4.0, 9.0 Hz, 1H), 7.16 (d,d, J=2.5, 10.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 2H).

Workup

  1. temperatureat reflux for 8 h
  2. customThe organic layer was separated
  3. washwashed with 1N HCl and brine (2x)
  4. dry with materialdried over MgSO4
  5. concentrationConcentration
  6. customgave a yellow oil which

Sources & evidence

ORD record
ord-95bc2c9af2cf43e6a821067270b70930
Source dataset
uspto-grants-1988_10
Patent number
US04775680

Reaction notes

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