Lithium Hydroxide → HCID 22280783, compound

HRID 1768109Notes

Reaction equation

HRID 1768109 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-44c564232c4244a08870489492506347
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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