Hydrochloric Acid → HCID 59533861, compound

HRID 221224Notes

Reaction equation

HRID 221224 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8](/[CH:11]=[C:12](\[C:18]3[CH:31]=[CH:30][C:29]4[S:28](=[O:33])(=[O:32])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21](C(OC(C)(C)C)=O)[C:20]=4[CH:19]=3)/[C:13]([O:15]CC)=[O:14])[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[Na+].Cl>CO.CC(C)=O>[O:33]=[S:28]1(=[O:32])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][C:20]2[CH:19]=[C:18](/[C:12](=[CH:11]\[CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)/[C:13]([OH:15])=[O:14])[CH:31]=[CH:30][C:29]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59533860HCID 59533860, compound

Product 1

HCID 59533861HCID 59533861, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

1.14 g of tert-butyl 2-[(E)-2-(1,4-dioxa-spiro[4.5]dec-8-yl)-1-ethoxycarbonylvinyl]-5,5-dioxo-5H-phenothiazine-10-carboxylate are dissolved in 130 ml of methanol, and 7.0 ml of a 2 M NaOH solution are added. The reaction mixture is heated at the boil under reflux for two hours. Methanol is removed under reduced pressure and the reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid. The precipitated solid is dissolved in 200 ml of ethyl acetate and dried over MgSO4, and the solvent is then removed under reduced pressure. The residue obtained in this manner is dissolved in 20 ml of acetone, and 4 ml of 50% strength hydrochloric acid solution are added. The reaction mixture is stirred at room temperature for 30 minutes. The acetone is removed under reduced pressure and the residue is taken up in 100 ml of water and 100 ml of ethyl acetate. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. This gives 840 mg of (E)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(4-oxocyclohexyl)acrylic acid.

Workup

  1. temperatureThe reaction mixture is heated at the boil
  2. temperatureunder reflux for two hours
  3. customMethanol is removed under reduced pressure
  4. additionthe reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid
  5. dissolutionThe precipitated solid is dissolved in 200 ml of ethyl acetate
  6. dry with materialdried over MgSO4
  7. customthe solvent is then removed under reduced pressure
  8. customThe residue obtained in this manner
  9. customThe acetone is removed under reduced pressure
  10. dry with materialThe organic phase is dried over MgSO4
  11. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-26067672e2454f39b6c8b88154d526d8
Source dataset
uspto-grants-2012_06
Patent number
US08207146B2

Reaction notes

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