Hydrogen Peroxide → 2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid

HRID 1830137Notes

Reaction equation

HRID 1830137 reaction equation
C(C1COC(=O)N1[C:14](=[O:32])[CH:15]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18])C1C=CC=CC=1.[OH:33]O.[Li+].[OH-]>C1COCC1.O>[CH:26]1([CH2:25][CH:15]([CH2:16][C:17]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:18])[C:14]([OH:32])=[O:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 220540901-(4-Benzyl-2-oxo-oxazolidin-3-yl)-2-cyclohexylmethyl-4-morpholin-4-yl-butane-1,4-dione

Product 1

HCID 218998342-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A 0.05 M solution of 1-(4-benzyl-2-oxo-oxazolidin-3-yl)-2-cyclohexylmethyl-4-morpholin-4-yl-butane-1,4-dione (1 g) in 3:1 —THF/H2O was treated at 0° C. with 8 equivalents of 30% H2O2 followed by 2.0 equivalents of LiOH. The resulting mixture was stirred at 0–25° C. until the substrate had been consumed (approximately 1 hour). The excess peroxide was quenched at 0° C. with a 10% excess of 1.5 N aqueous Na2SO3. After buffering to pH 9–10 with aqueous NaHCO3 and evaporation of the THF, the oxazolidone chiral auxiliary was recovered by MeCl2 extraction. The carboxylic acid was isolated by EtOAc extraction of the acidified (pH 1–2) aqueous phase, then recrystallized from EtOAc and hexane to yield 0.58 g of 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid; H1NMR (DMSO-δ): 12(1H, s, COOH), 3.6–3.3(8H, m), 2.8–2.3(3H, m), 1.8–1.1(l 1H, m), 0.9–0.7(2H, m); MS: 282.2(M−1), 284.1 (M+1).

Workup

  1. customhad been consumed (approximately 1 hour)
  2. customThe excess peroxide was quenched at 0° C. with a 10% excess of 1.5 N aqueous Na2SO3
  3. customAfter buffering to pH 9–10 with aqueous NaHCO3 and evaporation of the THF
  4. customthe oxazolidone chiral auxiliary was recovered by MeCl2 extraction

Sources & evidence

ORD record
ord-48ef3585939a4fff9f5dbbba86409eb9
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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