Lithium hydroxide, monohydrate → HCID 9934115, compound

HRID 1835136Notes

Reaction equation

HRID 1835136 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[C:4]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:3]1.O.[OH-].[Li+]>O1CCCC1.O.CO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[C:4]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:3]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23503280HCID 23503280, compound

Product 1

HCID 9934115HCID 9934115, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 4-{[2,6-dihydro-2-methyl-4(2-methylpropyl)-6-(1-naphthalenylmethyl)-1-oxo-1H-pyrrolo[3,4-d]pyridazin-7-yl]thio}butanoate (0.24 g) prepared as described in b) above was stirred with lithium hydroxide hydrate (0.060 g) in tetrahydrofuran-water-methanol (3:1:1) for 3 hours. The solution was evaporated and the resulting residue was partitioned between ethyl acetate and dilute hydrochloric acid. The organic layer was washed with brine, dried, and evaporated to a solid, which was chromatographed with ethyl acetate-isohexane to give, after crystallisation from ethyl acetate-cyclohexane, 4-{[2,6-dihydro-2-methyl-4(2-methylpropyl)-6-(1-naphthalenylmethyl)-1-oxo-1H-pyrrolo[3,4-d]pyridazin-7-yl]thio}butanoic acid (0.075 g).

Workup

  1. customThe solution was evaporated
  2. customthe resulting residue was partitioned between ethyl acetate and dilute hydrochloric acid
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated to a solid, which
  6. customwas chromatographed with ethyl acetate-isohexane
  7. customto give
  8. customafter crystallisation from ethyl acetate-cyclohexane, 4-{[2,6-dihydro-2-methyl-4(2-methylpropyl)-6-(1-naphthalenylmethyl)-1-oxo-1H-pyrrolo[3,4-d]pyridazin-7-yl]thio}butanoic acid (0.075 g)

Sources & evidence

ORD record
ord-2c48835d4eff4587a80e0a5c04383d15
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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