Methanol → HCID 178447182, compound

HRID 1369611Notes

Reaction equation

HRID 1369611 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([O:24]CC)[CH:6]([PH:10]([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)=[O:11])C(C)C)C.[OH-].[Na+].CO.[CH2:33]1[CH2:37]OC[CH2:34]1>>[OH:24][C:5]([CH2:6][PH:10]([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)=[O:11])([CH2:27][CH:33]([CH3:37])[CH3:34])[C:4]([OH:3])=[O:28]

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178472206HCID 178472206, compound

Product 1

HCID 178447182HCID 178447182, compound

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)phosphinoylmethyl-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-92014b0d53a84f3dad1c5499c5c14e17
Source dataset
uspto-grants-2003_06
Patent number
US06579890B1

Reaction notes

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