Lithium Hydroxide → HCID 19075863, compound

HRID 965263Notes

Reaction equation

HRID 965263 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>[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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19075802HCID 19075802, compound

Product 1

HCID 19075863HCID 19075863, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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--H2 0 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-2f3373d078924223906a656ae9aedf4e
Source dataset
uspto-grants-1998_06
Patent number
US05773465

Reaction notes

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