Lithium hydroxide, monohydrate → HCID 19356080, compound

HRID 377616Notes

Reaction equation

HRID 377616 reaction equation
O.[OH-].[Li+].C[CH:5]([CH2:9][CH2:10][S:11][C:12]1[N:13]([CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)[N:14]=[C:15]2[C:20]=1[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[O:23])[N:16]2[CH2:24][CH:25]([CH3:27])[CH3:26])[C:6]([OH:8])=[O:7]>O1CCCC1.O>[CH3:22][N:18]1[C:19](=[O:21])[C:20]2=[C:12]([S:11][CH2:10][CH2:9][CH2:5][C:6]([OH:8])=[O:7])[N:13]([CH2:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)[N:14]=[C:15]2[N:16]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:17]1=[O:23]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 19356083HCID 19356083, compound

Product 1

HCID 19356080HCID 19356080, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (80 mg) was added to a solution of methyl 4-[(4,5,6,7-tetrahydro-5-methyl-7-{2-methylpropyl}-2-{1-naphthalenylmethyl}-4,6-dioxo-2H-pyrazolo[3,4-d]pyrimidin-3-yl)thio]butanoic acid (250 mg) in tetrahydrofuran (20 ml) and water was then added to give a homogeneous solution. After 18 hours the reaction mixture was partitioned between ether and 2 M sodium hydroxide. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with ethyl acetate which was then dried over magnesium sulfate. The organic phase was concentrated in vacuo and recrystallised from cyclohexane:ethyl acetate to give the title compound (130 mg).

Workup

  1. additionwas then added
  2. customto give a homogeneous solution
  3. customAfter 18 hours the reaction mixture was partitioned between ether and 2 M sodium hydroxide
  4. extractionextracted with ethyl acetate which
  5. dry with materialwas then dried over magnesium sulfate
  6. concentrationThe organic phase was concentrated in vacuo
  7. customrecrystallised from cyclohexane

Sources & evidence

ORD record
ord-bbe9da66c75f46af88da8a4ee846226f
Source dataset
uspto-grants-2000_02
Patent number
US06028074

Reaction notes

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