Sodium Hydroxide → HCID 20610318, compound

HRID 1071275Notes

Reaction equation

HRID 1071275 reaction equation
[OH-].[Na+].O1CCOCC1.[CH2:9]([O:11][C:12](=[O:44])[C:13]([NH:37][C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])([CH2:19][C:20]1[O:24][N:23]=[C:22]([CH:25]2[CH2:29][CH2:28][CH2:27][N:26]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:21]=1)C(OCC)=O)[CH3:10]>C(OCC)(=O)C.S(=O)(=O)(O)O>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][CH:25]1[C:22]1[CH:21]=[C:20]([CH2:19][CH:13]([NH:37][C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[C:12]([O:11][CH2:9][CH3:10])=[O:44])[O:24][N:23]=1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 312751,4-DioxaneHCID 20610270HCID 20610270, compound

Product 1

HCID 20610318HCID 20610318, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide, 1M, (21.5 mL, 21.5 mmol) was added in portions over 30 minutes to a dioxane (22 mL) solution of 2-allyloxycarbonylamino-2-[3-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-isoxazol-5-ylmethyl]-malonic acid diethyl ester (10.95 g, 21.5 mmol). After stirring overnight, the reaction had not gone to completion. An additional 0.2 equivalents of 1M sodium hydroxide (4.2 mL, 4.2 mmol) was added and stirring continued for 3 hours. The reaction was diluted with ethyl acetate (50 mL) and 1M sulfuric acid (23 mL) was added dropwise at 0° C. The aqueous portion was extracted twice with ethyl acetate. The combined organic portions were dried over magnesium sulfate and concentrated in vacuo to give a the title compound. The crude product was used directly in the next step without separation of the unreacted diester. MS (Cl) m/z 382.2 (M−99).

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. additionwas added dropwise at 0° C
  4. extractionThe aqueous portion was extracted twice with ethyl acetate
  5. dry with materialThe combined organic portions were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7debdeded9ed4cf8a903318773d2854d
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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