Methanol → HCID 178447690, compound

HRID 965154Notes

Reaction equation

HRID 965154 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([O:24]CC)[C:6]([CH2:12][S:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1)([PH2:10]=[O:11])[CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+].CO>C1COCC1>[OH:24][C:5]([CH3:27])([C:6]([CH2:12][S:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1)([PH2:10]=[O:11])[CH:7]([CH3:9])[CH3:8])[C:4]([OH:28])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178472208HCID 178472208, compound

Product 1

HCID 178447690HCID 178447690, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Ethoxy) (quinolin-2-ylthiomethyl)-phosphinoyl-methyl-4-methylpentanoic acid ethyl ester (4.5 g) was dissolved in 100 mL THF and 12.5 mL of 2N NaOH was added together with enough methanol to make the solution homogeneous. After 18 hours the THF was removed by evaporation, the residue diluted with 50 mL H2O and washed with 50 mL ethyl acetate. The aqueous phase was then acidified to pH 4, and the product extracted with 50 mL ethyl acetate (2×). The ethyl acetate was washed with 20 mL brine, dried with MgSO4 and evaporated to yield 3.8 g of 2-(hydroxy) (quinolin-2-ylthiomethyl)-phosphinoyl-methyl-4-methylpentanoic acid as a yellow oil, MS: 368 (MH+).

Workup

  1. customAfter 18 hours the THF was removed by evaporation
  2. additionthe residue diluted with 50 mL H2O
  3. washwashed with 50 mL ethyl acetate
  4. extractionthe product extracted with 50 mL ethyl acetate (2×)
  5. washThe ethyl acetate was washed with 20 mL brine
  6. dry with materialdried with MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-557f30e8567a4508866a255fc045fb88
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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