Lithium hydroxide, monohydrate → HCID 56656209, compound

HRID 1778324Notes

Reaction equation

HRID 1778324 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:31]=[CH:30][C:21]2[C:22]3[CH:23]=[CH:24][O:25][C:26]=3[CH2:27][CH2:28][O:29][C:20]=2[C:19]=1[C:32]([O:34]C)=[O:33])(=[O:16])=[O:15])[CH3:2].O.[OH-].[Li+]>O.O1CCOCC1>[CH2:36]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:31]=[CH:30][C:21]2[C:22]3[CH:23]=[CH:24][O:25][C:26]=3[CH2:27][CH2:28][O:29][C:20]=2[C:19]=1[C:32]([OH:34])=[O:33])(=[O:15])=[O:16])[CH3:37]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66685692HCID 66685692, compound2×

Product 1

HCID 56656209HCID 56656209, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 8-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylate (Intermediate 50, 0.134 g) and lithium hydroxide monohydrate (0.159 g) in water (3.8 mL) and dioxane (3.8 mL) was sealed in a microwave vial and irradiated in the microwave at 130° C. for 30 minutes. The mixture was concentrated in vacuo, water was added and it was acidified to pH3 with formic acid. This was extracted into ethyl acetate, dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 2.5-10%. The resultant product was recrystallised from a mixture of DCM and ethyl acetate to give 8-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylic acid (0.036 g) as a white solid.

Workup

  1. customwas sealed in a microwave vial
  2. customirradiated in the microwave at 130° C. for 30 minutes
  3. concentrationThe mixture was concentrated in vacuo, water
  4. additionwas added
  5. extractionThis was extracted into ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by chromatography on silica
  10. washeluting with a mixture of methanol and DCM, with a gradient of 2.5-10%
  11. customThe resultant product was recrystallised from a mixture of DCM and ethyl acetate

Sources & evidence

ORD record
ord-46253e4ec77a44d39e8802f9ab296fa7
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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