Sodium Hydroxide → HCID 178452340, compound

HRID 16709Notes

Reaction equation

HRID 16709 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]2=[O:24])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C@H:8]2[CH2:9][CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]2)[C:12](=[O:24])[CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501173HCID 178501173, compound

Product 1

HCID 178452340HCID 178452340, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

t-Butyl 4-[trans-4-(methoxycarbonyl)cyclohexyl]-3-oxopiperazine-1-carboxylate (385 mg) obtained in Reference Example 71 (3) is dissolved in methanol (8 ml), and thereto is added 1 N aqueous sodium hydroxide solution (3.4 ml) under ice-cooling. The reaction solution is stirred at room temperature for 20 hours and concentrated under reduced pressure. Water and chloroform are poured to the residue, and aqueous layer is acidified by addition of 2 N hydrochloric acid. The organic layer is separated, washed with saturated brine and dried over sodium sulfate. The solvent is removed by evaporation under reduced pressure to give the title compound (375 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. additionWater and chloroform are poured to the residue, and aqueous layer
  4. additionis acidified by addition of 2 N hydrochloric acid
  5. customThe organic layer is separated
  6. washwashed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3cfdcd3ae1cd4dcda832ba6fde1a4899
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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