Lithium Hydroxide → HCID 20452648, compound

HRID 1809046Notes

Reaction equation

HRID 1809046 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]1[C:12](=[O:13])[CH:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10][CH2:9][S:8][CH2:7]1)C.[Li+].[OH-]>C1COCC1>[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH:11]1[CH2:10][CH2:9][S:8][CH2:7][N:6]([CH2:5][C:4]([OH:25])=[O:3])[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15591235HCID 15591235, compound

Product 1

HCID 20452648HCID 20452648, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxo-1,3-thiazepan-3-yl]acetate (181 mg, 0.50 mmol) [Karanewsky U.S. Pat. No. 4,460,579] in THF (2 mL) is added 1.0 N aqueous LiOH (0.55 mL, 0.55 mmol) and the reaction mixture is stirred at ambient temperature for 6 h. The reaction mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and concentrated in vacuo to provide the title compound.

Workup

  1. customThe reaction mixture is purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a00bdf2f4ab4708a8f0e31306eb7961
Source dataset
uspto-grants-2013_01
Patent number
US08362005B2

Reaction notes

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