Sodium Hydroxide → HCID 20610247, compound

HRID 433661Notes

Reaction equation

HRID 433661 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-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 1 M 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-50bde0f7f40c45ca92458d48d6c80bb5
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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