Hydrogen chloride-ethyl acetate → HCID 23121933, compound

HRID 1713487Notes

Reaction equation

HRID 1713487 reaction equation
[CH:1]1([C:7]2([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:11]3[CH2:12][N:13](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:14][CH2:15][N:10]3[C:9](=[O:35])[O:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>O1CCCC1>[CH:36]1([C:7]2([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:35])[O:8]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 23121954HCID 23121954, compound

Product 1

HCID 23121933HCID 23121933, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-dicyclohexyl-7-(triphenylmethyl)-3H-oxazolo[3,4-a]pyrazin-3-one (0.92 g, 1.7 mmol) in tetrahydrofuran (5 mL) was added a 4 M hydrogen chloride/ethyl acetate solution (5 mL) with ice cooling, and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was concentrated under reduced pressure, water was then added thereto and washed with diethyl ether. To the aqueous layer was added sodium hydrogen carbonate, and the mixture was adjusted to pH 7 and then extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The precipitated crystals were washed with hexane and dried to obtain the title compound (0.41 g, yield 80%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas then added
  3. washwashed with diethyl ether
  4. additionTo the aqueous layer was added sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. concentrationconcentrated under reduced pressure
  8. washThe precipitated crystals were washed with hexane
  9. customdried

Sources & evidence

ORD record
ord-5f0512565904462ca96f7abe73533a0e
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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