Sodium Hydroxide → HCID 11070700, compound

HRID 1857993Notes

Reaction equation

HRID 1857993 reaction equation
[CH2:1]([N:8]1[CH:15]([CH2:16][CH2:17][CH:18]2OCCCO2)[CH2:14][CH:13]2[CH:9]1[CH2:10][N:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[N:31]1([C:36]2[CH:41]=[CH:40][C:39]([NH:42]N)=[CH:38][CH:37]=2)[CH:35]=[CH:34][N:33]=[CH:32]1.[OH-].[Na+]>OS(O)(=O)=O>[CH2:1]([N:8]1[CH:15]([CH2:16][C:17]2[C:40]3[C:39](=[CH:38][CH:37]=[C:36]([N:31]4[CH:35]=[CH:34][N:33]=[CH:32]4)[CH:41]=3)[NH:42][CH:18]=2)[CH2:14][CH:13]2[CH:9]1[CH2:10][N:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10883617HCID 10883617, compoundHCID 67652043HCID 67652043, compound

Product 1

HCID 11070700HCID 11070700, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of (1RS,3RS,5RS)-2-benzyl-3-[2-(1,3-dioxan-2-yl)ethyl]-2,7-diazabicyclo[3.3.0]octane-7-carboxylic acid, ethyl ester (0.3081 g, 0.793 mmol) and 4-(imidazol-1-yl)phenylhydrazine, dihydrochloride (0.2055 g, 0.832 mmol) in 4% H2SO4 (aq) (10 mL) was heated at reflux under argon for 20 h whilst stirring magnetically. After cooling, the reaction mixture was made basic with 50% NaOH solution and extracted with EtOAc (4×25 mL). The combined organic extracts were dried (K2CO3) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 2-4% MeOH/CH2Cl2) to give 0.1625 g (44%) of the title compound as a yellow gum. δH (250 MHz, CDCl3) 1.23-1.26 (3H, m), 1.56-1.68 (1H, m), 1.92 (1H, m), 2.56 (1H, m), 2.79 (1H, m), 3.14 (1H, dd), 3.17-3.78 (7H, m), 4.07-4.13 (3H, m), 7.10-7.34 (11H, m), 7.74 (1H, s), 8.24 (1H, br s). m/e (ES+) 470 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 20 h
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc (4×25 mL)
  5. dry with materialThe combined organic extracts were dried (K2CO3)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 2-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d006906d44e943468eef28561174625e
Source dataset
uspto-grants-2000_11
Patent number
US06150391

Reaction notes

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