Sodium Hydroxide → HCID 10720002, compound

HRID 861756Notes

Reaction equation

HRID 861756 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][N:18]1[CH2:23][CH2:22][C:21](=[C:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH:28]=[CH:27][C:26]3[CH:35]=[CH:36][CH:37]=[CH:38][C:25]2=3)[CH2:20][CH2:19]1)[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][N:18]1[CH2:23][CH2:22][C:21](=[C:24]2[C:25]3[CH:38]=[CH:37][CH:36]=[CH:35][C:26]=3[CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=3)[CH2:20][CH2:19]1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10577584HCID 10577584, compound

Product 1

HCID 10720002HCID 10720002, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl (S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin-1-yl]propionate(2 g, 3.9 mmol) in 30 ml ethanol was added 10 ml of 1N NaOH aqueous solution. The mixture was then stirred at room temperature for 3 hours. After removing most ethanol under reduced pressure, the remaining mixture was diluted with ice-water and neutralized with acetic acid. The mixture was then extracted with chloroform (2×30 ml). The combined chloroform extract was washed with saline and dried over Na2SO4. After evaporating to dryness, the solid residue was recrystallized from ethanol to afford the title compound as a white crystalline. Yield:1.77 g (91%)

Workup

  1. customAfter removing most ethanol under reduced pressure
  2. additionthe remaining mixture was diluted with ice-water and neutralized with acetic acid
  3. extractionThe mixture was then extracted with chloroform (2×30 ml)
  4. extractionThe combined chloroform extract
  5. washwas washed with saline
  6. dry with materialdried over Na2SO4
  7. customAfter evaporating to dryness
  8. customthe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-fb525512da824bc8b64f667bc7512aa5
Source dataset
uspto-grants-1998_02
Patent number
US05714501

Reaction notes

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