Lithium Hydroxide → HCID 21109742, compound

HRID 1766197Notes

Reaction equation

HRID 1766197 reaction equation
[OH-].[Li+].[O:3]=[C:4]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]2=[O:36])[CH2:22][CH2:21]1)/[CH:5]=[CH:6]/[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=1.CO.CC(O)=O.[K+].[Br-]>O.C1COCC1>[O:3]=[C:4]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]2=[O:36])[CH2:22][CH2:21]1)/[CH:5]=[CH:6]/[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 253877Potassium BromideHCID 10129899Acetic acid methanolHCID 21109743HCID 21109743, compound

Product 1

HCID 21109742HCID 21109742, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.24 g (10.0 mmol) of lithium hydroxide in 20 ml of water was added to a solution of 1.2 g (2.6 mmol) of (E)-3,4-dihydro-3-{1-[1,4-dioxo-4-(4-ethoxycarbonylphenyl)-2-buten-1-yl]-4-piperidinyl}-2(1H)-quinazolinone (Item no. 169) in 20 ml of THF. After stirring for 4 hours at ambient temperature the mixture was diluted with 200 ml of water and extracted once with 100 ml of tert.butylmethylether. The aqueous phase was acidified with 1N hydrochloric acid and extracted five times with a mixture of dichloromethane and methanol (9/1 v/v). The combined organic extracts were dried over sodium sulphate and concentrated by evaporation in vacuo. The residue remaining was triturated with diethylether and suction filtered. After drying in a circulating air dryer 0.5 g (44% of theoretical) of colourless crystals were obtained. Rf 0.72 (EE/MeOH/AcOH 80/20/5 v/v/v) or 0.43 (El D). IR (KBr): 1689 (C═O) MS: no M+

Workup

  1. extractionextracted once with 100 ml of tert.butylmethylether
  2. extractionextracted five times
  3. additionwith a mixture of dichloromethane and methanol (9/1 v/v)
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe residue remaining was triturated with diethylether and suction
  7. filtrationfiltered
  8. customAfter drying in a circulating air dryer 0.5 g (44% of theoretical) of colourless crystals
  9. customwere obtained

Sources & evidence

ORD record
ord-a3e42238476142cd8e37ebd03b4df5e7
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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