Lithium Hydroxide → 3-[[(4-Methoxy)tetrahydropyran-4-yl]phenylmethyl-thio]propionic acid

HRID 890888Notes

Reaction equation

HRID 890888 reaction equation
[CH3:1][O:2][C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Li+].[OH-]>O.CO>[CH3:1][O:2][C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54047158Methyl 3-[[(4-methoxy)-tetrahydro-pyran-4-yl]phenylmethylthio]propionate

Product 1

HCID 537565113-[[(4-Methoxy)tetrahydropyran-4-yl]phenylmethyl-thio]propionic acidYield 103.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 3-[[(4-methoxy)tetrahydropyran-4-yl]phenyl-methyl-thio]propionate (Step 1) (0.91 g, 2.8 mmol) and LiOH (0.29 g, 7.01 mmol) in 10% water and methanol (10 mL) was stirred for 18 h at room temperature. The solvents were removed at reduced pressure, and the concentrated residue was partitioned between ethyl acetate (200 mL) and 1 N HCl (100 mL). The organic layer was separated and washed with saturated brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was vacuum dried to give 0.9 g of 3-[[(4-methoxy)tetrahydropyran-4-yl]phenylmethyl-thio]propionic acid as a clear, colorless oil: HRMS calcd for C16H22O4S 310.1239, found 310.1241.

Workup

  1. customThe solvents were removed at reduced pressure
  2. customthe concentrated residue was partitioned between ethyl acetate (200 mL) and 1 N HCl (100 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated brine (1×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-461a31ab2aa34ef59078edf5c6372745
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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