Hydrogen Peroxide → HCID 76652353, compound

HRID 1666945Notes

Reaction equation

HRID 1666945 reaction equation
C(C1COC(=O)N1[C:14](=[O:33])[CH:15]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:16][N:17]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH:18]=[O:19])C1C=CC=CC=1.C1C[O:37]CC1.O.OO>[Cl-].[Na+].O>[CH:28]1([CH2:27][CH:15]([CH2:16][N:17]([CH:18]=[O:19])[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:14]([OH:33])=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8028TetrahydrofuranHCID 76652336HCID 76652336, compound

Product 1

HCID 76652353HCID 76652353, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

N-[3-(4-Benzyl-2-oxo-oxazolidin-3-yl)-2-cyclopentylmethyl-3-oxo-propyl]-N-(tetrahydro-pyran-2-yloxy)-formamide (3.65 g, 7.96 mmol), THF (125 mL), and water (40 mL) is cooled to 4° C. To this mixture, is added 30% H2O2 (5.2 mL, 50.90 mmole) and LiOH monohydrate (0.40 g, 9.53 mmol), respectively. The reaction mixture is stirred for 1.5 hours. The mixture is slowly quenched with 0.5 M Na2SO3, while maintaining the temperature below 15° C. with an ice bath. The quenched mixture is stirred for an addition 30 minutes, concentrated in vacuo until the THF solvent is removed, and washed with EtOAc. The basic reaction mixture is acidified with Amberlite IR-120 resin (H+) to pH=4.5. Brine is added to the acidic solution, and the combined mixture is extracted with EtOAc. The organic layers from the acidic solution washing are combined, dried over Na2SO4, and concentrated in vacuo. This gave 2-cyclopentylmethyl-3-[formyl-(tetrahydro-pyran-2-yloxy)-amino]-propionic acid (1.20 g, 50% yield) as an oil.

Workup

  1. customThe mixture is slowly quenched with 0.5 M Na2SO3
  2. temperaturewhile maintaining the temperature below 15° C. with an ice bath
  3. stirringThe quenched mixture is stirred for an addition 30 minutes
  4. concentrationconcentrated in vacuo until the THF solvent
  5. customis removed
  6. washwashed with EtOAc
  7. customThe basic reaction mixture
  8. extractionthe combined mixture is extracted with EtOAc
  9. washThe organic layers from the acidic solution washing
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d479f233d234e30afb754b6953a8c0a
Source dataset
uspto-grants-2011_10
Patent number
US08044199B2

Reaction notes

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