Ethanol → HCID 58815934, compound

HRID 2245886Notes

Reaction equation

HRID 2245886 reaction equation
C([O:3][C:4](=[O:39])[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:19]([N:27]3[CH2:32][C@@H:31]([CH3:33])[N:30]([CH2:34][CH:35]=[CH2:36])[CH2:29][C@@H:28]3[CH3:37])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[CH:14]=2)[CH2:8][CH2:7]1)C.C(O)C.[OH-].[Na+].S(=O)(=O)(O)O>O>[CH2:34]([N:30]1[C@H:31]([CH3:33])[CH2:32][N:27]([C@@H:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[C:12]([N:9]2[CH2:8][CH2:7][C:6](=[CH:5][C:4]([OH:39])=[O:3])[CH2:11][CH2:10]2)=[O:38])[C@@H:28]([CH3:37])[CH2:29]1)[CH:35]=[CH2:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58815941HCID 58815941, compound

Product 1

HCID 58815934HCID 58815934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preceding ester, Example 137, was hydrolyzed as follows. A 50 mL round bottom flask equipped with a magnetic stir bar was charged with 0.64 g (1.2 mmol, 1 eq) of (1-{3-[(R)-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)(3-hydroxyphenyl)methyl]-benzoyl}-4-piperidinylidene)acetic acid ethyl ester, 5.0 mL ethanol, and 3.0 mL (6 mmol, 5 eq) of 2 N aqueous NaOH solution. The reaction was stirred at room temperature for 3 days and neutralized with 3.0 mL (6 mmol, 5 eq) of 2 N aqueous sulfuric acid. After stirring for 30 minutes, the reaction was filtered to remove the sodium sulfate and the solvent was removed in vacuo. The residue was dissolved in 5 mL of ethanol and filtered through a 0.2 □m polypropylene membrane. The filtrate was concentrated in vacuo, leaving an off-white solid. This material was dissolved in 8 mL of water, filtered through a 0.2 □m polypropylene membrane, and lyophilized to give (1-{3-[(R)-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)(3-hydroxyphenyl)methyl]-benzoyl}-4-piperidinylidene)acetic acid as a fluffy, white solid, 0.598 g. Calculated for C30H37N3O4 0.25 H2SO4 2.0 H2O: %C, 63.87; H, 7.41; N, 7.45. Found: %C, 64.03; H, 7.31; N, 7.42. 1H NMR (300 MHz, D2O with ˜0.1 N NaOD): {tilde over (□)}□brd, J=7.6 Hz, 1H), 7.30-7.25 (m, 2H), 7.14 (d, J=7.2 Hz, 1H), 6.93 (t, J=7.7 Hz, 1H), 6.46-6.37 (m, 2H), 6.29 (d, J=7.3 Hz, 1H), 5.77-5.66 (m, 1H), 5.61 (d, J=13.3 Hz, 1H), 5.10 (d, J=8.3 Hz, 1H), 5.07 (s, 2H), 3.72-3.51 (m, 2H), 3.26-3.22 (m, 3H), 2.76-2.21 (series of m, 8H), 2.02 (brt, 2H), 1.91 (brt, 1H, 0.96 (d, J=6.1 Hz, 3H), 0.82 (d, J=6.1 Hz, 3H).

Workup

  1. customA 50 mL round bottom flask equipped with a magnetic stir bar
  2. stirringAfter stirring for 30 minutes
  3. filtrationthe reaction was filtered
  4. customto remove the sodium sulfate
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in 5 mL of ethanol
  7. filtrationfiltered through a 0.2 □m polypropylene membrane
  8. concentrationThe filtrate was concentrated in vacuo
  9. customleaving an off-white solid
  10. filtrationfiltered through a 0.2 □m polypropylene membrane

Sources & evidence

ORD record
ord-a271c878e286417ca5511accc36e2806
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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