Water → HCID 86588455, compound

HRID 983398Notes

Reaction equation

HRID 983398 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:12][CH2:11][N:10]([C@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:14])[C:9]2=O)=O)[N:3]=[CH:2]1.Cl.[CH2:23]([O:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH2:32]>N1C=CC=CC=1>[CH2:23]([O:30][N:31]=[C:6]([C:4]1[N:3]=[CH:2][O:1][CH:5]=1)[CH:8]1[CH2:9][N:10]([C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[C:11](=[O:32])[CH2:12]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 102312Benzyloxyamine hydrochlorideHCID 86588456HCID 86588456, compound

Product 1

HCID 86588455HCID 86588455, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(Oxazole-4-carbonyl-1-((S)-1-phenylethyl)pyrrolidin-2-one (0.5 g, 1.76 mmol) [Example 6B1] and O-benzylhydroxylamine, hydrochloride (0.42 g, 2.64 mmol) in pyridine (5 mL) were refluxed for five hours and then cooled to room temperature. The reaction mixture was diluted with water, washed with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with a mixture of 1:2 mixture of hexanes:ethyl acetate to provide 0.41 g of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.75-7.60 (m, 1H), 7.40-7.12 (m, 11H), 5.60-5.45 (m, 1H), 5.35-5.23 (m, 1H), 5.20-5.08 (m, 1H), 4.30-4.16 (m, 1H), 3.88-2.60 (m, 4H), 1.50-1.30 (m, 3H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with a mixture of 1:2 mixture of hexanes

Sources & evidence

ORD record
ord-b72acafe337e4c90b85667fdaae9e41f
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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