Hydrochloric Acid → HCID 20610283, compound

HRID 433821Notes

Reaction equation

HRID 433821 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH:5]([NH:29][C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:6][C:7]1[O:11][N:10]=[C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:28])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH:8]=1)[CH3:2].Cl.[OH-].[Na+]>C(O)C.O.[Fe]>[CH2:1]([O:3][C:4](=[O:36])[CH:5]([NH:29][C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:6][C:7]1[O:11][N:10]=[C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:28])[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20610284HCID 20610284, compound

Product 1

HCID 20610283HCID 20610283, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 2-allyloxycarbonylamino-3-(3-{1-[(4-nitro-phenyl)-acetyl]-pyrrolidin-2-yl}-isoxazol-5-yl)-propionic acid ethyl ester (2B) (565 mg, 1.13 mmol) and iron(0) powder (384 mg, 6.98 mmol) in ethanol/water (5 mL, 1:1) was heated to reflux. Hydrochloric acid, 1M, (0.29 mL, 0.29 mmol) was added drop wise and the reaction was heated at reflux for 45 minutes. It was then neutralized with 1M sodium hydroxide and filtered through celite. The filtrate was diluted with ethyl acetate and washed with water and brine. The organic portion was dried over magnesium sulfate and concentrated in vacuo. The crude residue was chromatographed on a Biotage Flash 40S column eluting with ethyl acetate/hexanes (6:1) to provide the title compound as a yellow oil (240 mg, 51%). MS (CI) m/z 471.0 (M+1)

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 45 minutes
  3. filtrationfiltered through celite
  4. additionThe filtrate was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialThe organic portion was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was chromatographed on a Biotage Flash 40S column
  9. washeluting with ethyl acetate/hexanes (6:1)

Sources & evidence

ORD record
ord-8967325dfeec4439a58ca6005e99933e
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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