Lithium Hydroxide → HCID 19075863, compound

HRID 2257241Notes

Reaction equation

HRID 2257241 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)([C:18]([O:20]CC)=[O:19])[C:13]([O:15]CC)=[O:14].[Li+].[OH-]>CO.CO.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)([C:13]([OH:15])=[O:14])[C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19075802HCID 19075802, compound

Product 1

HCID 19075863HCID 19075863, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of ethyl 3-(quinolin-2-yl)-2-(2-tetrahydropyranyloxy)-2-ethoxycarbonyl-propanoate (0.5 g) in 5 ml of methanol is hydrolysed by treatment with a LiOH in MeOH-H2O solution. After 12 h at r.t., the solvent is evaporated off under vacuum and the residue is partitioned between AcOEt and an excess of a monobasic potassium phosphate saturated solution. The organic phase is separated, dried, evaporated to dryness to obtain 0.39 g of 3-(quinolin-2-yl)-2-(2-tetrahydropyranyloxy)-2-carboxy-propanoic acid.

Workup

  1. customthe solvent is evaporated off under vacuum
  2. customthe residue is partitioned between AcOEt
  3. customThe organic phase is separated
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8828d96d1f094fef8fa232209916b675
Source dataset
uspto-grants-1997_08
Patent number
US05656656

Reaction notes

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