Lithium Hydroxide → HCID 22280783, compound

HRID 968354Notes

Reaction equation

HRID 968354 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-feb1121331fb47679b4c9310b90865a8
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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