Sodium ethoxide → HCID 53722639, compound

HRID 1734877Notes

Reaction equation

HRID 1734877 reaction equation
[O-]CC.[Na+].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@H:17]([O:25]C(=O)C2C=CC=CC=2)[CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][C:10]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:8])([CH3:7])[CH3:6]>>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@H:17]([OH:25])[CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:11][C:10]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:43]=2[O:44][C:45]2[C:50]1=[CH:49][CH:48]=[CH:47][CH:46]=2)([CH3:8])([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 53898217HCID 53898217, compound

Product 1

HCID 53722639HCID 53722639, compoundYield 85%

Procedure

13.3 ml of a 0.58M ethanolic solution of sodium ethoxide were added to 1.62 g (2.57 mmol) of (S)-N-[2-t-butyl-5-(4-cyclohexyl-3-benzoyloxybutyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 101), and the resulting mixture was stirred at room temperature for 8 hours, after which it was heated under reflux for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with water and then extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 150 g of silica gel, using a 2:8 by volume mixture of acetonitrile and benzene as the eluent. The concentrated eluate was recrystallized from diisopropyl ether, to give 1.14 g (yield 85%) of the title compound, melting at 141° -142° C.

Workup

  1. temperatureafter which it was heated
  2. temperatureunder reflux for 2 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. additionthe resulting residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe residue was purified by column chromatography through 150 g of silica gel
  10. additionby volume mixture of acetonitrile and benzene as the eluent
  11. customThe concentrated eluate was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d3f14fc1b1f54613862374ab6f39e778
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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