Lithium Hydroxide → HCID 69969807, compound

HRID 2289115Notes

Reaction equation

HRID 2289115 reaction equation
C(O[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[C:21]([CH2:29][CH3:30])=[N:22][O:23][C:24]=3[C:25]=2[CH2:26][CH2:27][CH3:28])=[C:8](C)[C:7]=1[CH3:32])(=O)CC.[Li+].[OH-:34]>CO>[CH3:32][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[C:21]([CH2:29][CH3:30])=[N:22][O:23][C:24]=3[C:25]=2[CH2:26][CH2:27][CH3:28])[CH:10]=[CH:11][C:6]=1[CH:8]([CH3:7])[C:9]([OH:12])=[O:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69969348HCID 69969348, compound

Product 1

HCID 69969807HCID 69969807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of methyl-2-methyl-4-(3-(3-(Ethyl)-7-(propyl)-6-benz-[4,5]-isoxazoloxy)propyloxy)-phenyl propionate (11.5 mg, Step A) was dissolved in MeOH (0.5 mL)and 1M LiOH (0.10 mL) was added. The resulting solution was warmed to 50° C. for 2 hours, cooled and concentrated. The residue was partitioned between ethyl acetate and 1 M Hcl. The organic fraction was removed, dried and concentrated to give the title compound as a colorless oil (10.7 mg) NMR (CDCl3); δ 7.40 (d,2H), 7.11 (d,2H), 6.95 (d,2H), 6.85 (d,2H), 1.43 (t,3H), 1.18 (d,2H), 0.95 (t,3H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and 1 M Hcl
  4. customThe organic fraction was removed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cad9cb877fcc47b08ce7452f864ca09d
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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