Hydrochloric Acid → HCID 54346537, compound

HRID 1734882Notes

Reaction equation

HRID 1734882 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C@@H:13]([O:24]COC)[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:7][C:6]=1[NH:28][C:29](=[O:45])[CH2:30][CH:31]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:38][C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C@@H:13]([OH:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[CH:7][C:6]=1[NH:28][C:29](=[O:45])[CH2:30][CH:31]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:38][C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53911007HCID 53911007, compound

Product 1

HCID 54346537HCID 54346537, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.20 g (1.96 mmol) of (S)-N-{2-t-butyl-5-[7-cyclohexyl-3-(methoxymethoxy)heptyl]phenyl}-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 43) in 12 ml of a 4N solution of hydrogen chloride in dioxane was stirred for 30 minutes and then the solvent was removed by distillation under reduced pressure. The pH of the residue was brought to 7 by adding an aqueous solution of sodium hydrogencarbonate, and the resulting mixture was extracted twice with ethyl acetate. The combined extracts were washed with a saturated aqueous solution of sodium chloride. The washed extracts were dried, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.9 g of the title compound as an oil. This oil was triturated with hexane and the resulting crystallized product was collected, to give 0.83 9 (yield 75%) of the title compound as crystals.

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. additionby adding an aqueous solution of sodium hydrogencarbonate
  3. extractionthe resulting mixture was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
  5. customThe washed extracts were dried
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-b16bc44556e3417f900129f90e3f3615
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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