Water → HCID 68898768, compound

HRID 2099702Notes

Reaction equation

HRID 2099702 reaction equation
C([O:3][C:4]([CH:6]1[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH3:17])=[CH:14][C:8]=2[O:7]1)=[O:5])C.O.O.[OH-].[Li+]>C1COCC1.CO>[C:23]([O:22][C:20]([N:18]([CH3:19])[CH:16]([CH3:17])[CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][CH:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:14]=1)=[O:21])([CH3:25])([CH3:26])[CH3:24]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 688992145-[2-(Tert-butoxycarbonyl-methyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic acid ethyl ester

Product 1

HCID 68898768HCID 68898768, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 21 mg (0.06 mmol) of 1D in 0.5 mL of THF, 0.5 mL of methanol, and 1 mL of water was added 50 mg (1.19 mmol) of lithium hydroxide monohydrate as solid. The reaction mixture was allowed to stir at room temperature for 2.5 hours and concentrated to dryness. To the residue, 10 mL of water was added, and pH of the resulting mixture was adjusted to 2 using phosphoric acid. This was extracted with 3×35 mL of ethyl acetate. Organic layers were combined, dried (anhydrous Na2SO4) and concentrated to dryness to give 10 mg (0.029 mmol, 53%) of 1M (M+Na, 360).

Workup

  1. concentrationconcentrated to dryness
  2. additionTo the residue, 10 mL of water was added
  3. extractionThis was extracted with 3×35 mL of ethyl acetate
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated to dryness
  6. customto give 10 mg (0.029 mmol, 53%) of 1M (M+Na, 360)

Sources & evidence

ORD record
ord-5490e6b546a144b99e8cf5f60ab58926
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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