Sodium Hydroxide → HCID 22125680, compound

HRID 1857995Notes

Reaction equation

HRID 1857995 reaction equation
[CH3:1][N:2]1[CH:9]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N:20]4[CH:24]=[N:23][N:22]=[CH:21]4)[CH:18]=3)[NH:13][CH:12]=2)[CH2:8][CH:7]2[CH:3]1[CH2:4][N:5](C(OCC)=O)[CH2:6]2.[OH-].[Na+]>Cl>[CH3:1][N:2]1[CH:9]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N:20]4[CH:24]=[N:23][N:22]=[CH:21]4)[CH:18]=3)[NH:13][CH:12]=2)[CH2:8][CH:7]2[CH:3]1[CH2:4][NH:5][CH2:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86756045HCID 86756045, compound

Product 1

HCID 22125680HCID 22125680, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (1RS,3RS,5RS)-2-methyl-3-[{5-(1,2,4-triazol-4-yl)-1H-indol-3-yl}methyl]-2,7-diazabicyclo[3.3.0]octane-7-carboxylic acid, ethyl ester (0.3452 g, 0.875 mmol) in concentrated hydrochloric acid (10 mL) was heated at reflux for 40 h, whilst stirring magnetically. After cooling, the reaction mixture was basified with 50% NaOH solution (8 mL) and extracted with CH2Cl2 (4×75 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (alumina, CH2Cl2 --MeOH--NH3 (aq); 90:10:1) to give 0.2367 g (84%) of the title compound as a yellow gum. δH (360 MHz, CDCl3) 1.42 (1H, m), 1.87 (1H, m), 2.43-2.59 (2H, m), 2.54 (3H, s), 2.66 (1H, d, J=11.1 Hz), 2.77 (1H, m), 2.81-2.86 (1H, m), 2.99 (1H, m), 3.13 (1H, dd, J=3.7 and 14.2 Hz), 3.29 (1H, m), 3.46 (1H, m), 7.14-7.17 (2H, m), 7.49 (1H, d, J=8.4 Hz), 7.52 (1H, d, J=2.0 Hz), 8.47 (2H, s), 8.58 (1H, br s). m/e (ES+) 323 (M+H)+.

Workup

  1. temperatureat reflux for 40 h
  2. temperatureAfter cooling
  3. extractionextracted with CH2Cl2 (4×75 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (alumina, CH2Cl2 --MeOH--NH3 (aq); 90:10:1)

Sources & evidence

ORD record
ord-51322eaff8d0480db7db02bbd31bc474
Source dataset
uspto-grants-2000_11
Patent number
US06150391

Reaction notes

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