Hydrochloric Acid → HCID 18539790, compound

HRID 411115Notes

Reaction equation

HRID 411115 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][C:13]2[CH2:17][CH2:16][O:15][N:14]=2)=[C:10]([CH:18]=[S:19](=[O:21])=[O:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+].Cl>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[C:11]([CH2:12][C:13]2[CH2:17][CH2:16][O:15][N:14]=2)=[C:10]([CH:18]=[S:19](=[O:20])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18539782HCID 18539782, compound

Product 1

HCID 18539790HCID 18539790, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 5° C., a solution of 2.3 g (7 mmol) of methyl 2-chloro-3-(4,5-dihydro-3-isoxazolylmethyl)-4-sulfonylmethylbenzoate in 40 ml of tetrahydrofuran is treated with 0.3 g (13 mmol) of lithium hydroxide. The reaction mixture is taken up in 300 ml of diethyl ether and adjusted to pH 1 using 10% strength aqueous hydrochloric acid. The aqueous phase is extracted with diethyl ether. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 1.7 g; 1H NMR, δ [ppm], DMSO-d6; 3.0 (t), 3.3 (s), 4.2 (t), 4.3 (s), 7.8 (d), 8.1 (d).

Workup

  1. extractionThe aqueous phase is extracted with diethyl ether
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-7328cc98396e465baf0839deba799a68
Source dataset
uspto-grants-2003_05
Patent number
US06559100B1

Reaction notes

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