Lithium Hydroxide → HCID 22280783, compound

HRID 1071479Notes

Reaction equation

HRID 1071479 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH2:14][C:13]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])([C:15]([O:17]C)=[O:16])[O:12][N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[Li+].[OH-]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH2:14][C:13]([CH2:19][NH:20][S:21]([CH3:24])(=[O:22])=[O:23])([C:15]([OH:17])=[O:16])[O:12][N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22280772HCID 22280772, compound

Product 1

HCID 22280783HCID 22280783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-cyano-4-fluorophenyl)-5-(methylsulfonylaminomethyl)-5-(carbomethoxy)isoxazoline (1.13 g) in THF (50 mL) was added LiOH (3.50 mL of 1N aqueous solution). The mixture was stirred at RT under N2 for ½ h. The solvent was removed, the resulting material was diluted with water and acidified with concentrated HCl. It was then extracted with EtOAc, and the organic solution was dried over MgSO4 and concentrated to a light yellow foam (0.98 g). 1H NMR (DMSO-d6) δ 8.17 (m, 2H), 7.56 (t, 1H), 3.98-3.79 (m, 2H), 3.69 (bs, 2H), 3.01 (s, 3H) ppm; ESI mass spectrum z (rel. intensity) 339.8 (M−H, 100).

Workup

  1. customThe solvent was removed
  2. additionthe resulting material was diluted with water
  3. extractionIt was then extracted with EtOAc
  4. dry with materialthe organic solution was dried over MgSO4
  5. concentrationconcentrated to a light yellow foam (0.98 g)

Sources & evidence

ORD record
ord-5024917979fc480b96e09fddb41b5790
Source dataset
uspto-grants-2005_06
Patent number
US06906070B2

Reaction notes

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