Sodium Hydroxide → HCID 67148128, compound

HRID 1054011Notes

Reaction equation

HRID 1054011 reaction equation
C([O:3][C:4](=[O:47])[CH2:5][CH2:6][C:7]1[O:8][C:9]2[CH:46]=[CH:45][CH:44]=[CH:43][C:10]=2[C:11]=1[CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18](=[O:42])[CH:19]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])C.[OH-].[Na+]>C1COCC1>[CH2:27]([O:26][C:24]([NH:23][CH2:22][CH2:21][CH2:20][CH:19]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][CH:13]1[CH2:12][C:11]1[C:10]2[CH:43]=[CH:44][CH:45]=[CH:46][C:9]=2[O:8][C:7]=1[CH2:6][CH2:5][C:4]([OH:47])=[O:3])=[O:42])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67148581HCID 67148581, compound

Product 1

HCID 67148128HCID 67148128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing the crude 53 (3.0 g, 4.6 mmol) in THF (20 mL) was treated with 3 M NaOH (8 mL) at ambient temperature. The reaction mixture was then warmed to gentle reflux and maintained for 2.5 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc. The organic solution was washed with 1 N HCl then dried over anhydrous Na2SO4, filtered and concentrated to afford ˜3 g (quant.) of 54 as an off-white-colored foam which was used directly without further purification. 1H NMR (CDCl3, 300 MHz) δ7.69-7.67 (m, 1H), 7.39-7.20 (m, 8H), 5.70 (d, J=8.4 Hz, 1H), 5.13-5.09 (m, 2H), 4.50-4.45 (m, 1H), 3.67-3.54 (m, 1H), 3.22-3.18 (m, 2H), 3.13 (t, J=6.9 Hz, 1H), 2.85-2.78 (m, 2H), 2.09-1.97 (m, 3H), 1.76-1.62 (m, 4H), 1.43 (s, 9H) ppm.

Workup

  1. temperatureThe reaction mixture was then warmed
  2. temperatureto gentle reflux
  3. temperaturemaintained for 2.5 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in EtOAc
  6. washThe organic solution was washed with 1 N HCl
  7. dry with materialthen dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6f8b5556e49a49f59e23f91a3c7f40c1
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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