Sodium Hydroxide → HCID 20610247, compound

HRID 433818Notes

Reaction equation

HRID 433818 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:14]([O:16]CC)=[O:15])[CH3:10]>C(OCC)(=O)C.S(=O)(=O)(O)O>[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]([CH3:35])([CH3:36])[CH3:34])=[O:31])[CH:21]=1)[C:14]([OH:16])=[O:15])[CH3:10]

Participants

6

Reactant 3

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

Product 1

HCID 20610247HCID 20610247, 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-butoxycarbonylpyrrolidin-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 (CI) 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-39706f214f174d55abf6b53885542624
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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