Lithium Hydroxide → HCID 60828526, compound

HRID 424628Notes

Reaction equation

HRID 424628 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:24])[CH2:7][N:8]([CH:21]1[CH2:23][CH2:22]1)[S:9]([C:12]1[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=1[Cl:20])(=[O:11])=[O:10])C>O.C1COCC1>[CH:21]1([N:8]([CH2:7][C:6]([OH:24])=[O:5])[S:9]([C:12]2[C:13]([Cl:20])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=2[Cl:18])(=[O:11])=[O:10])[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66703404HCID 66703404, compound

Product 1

HCID 60828526HCID 60828526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A soln. of lithium hydroxide (298 mg, 12.5 mmol) in water (15 ml) was added to a soln. of [cyclopropyl-(2,4,6-trichlorobenzenesulfonyl)-amino]-acetic acid ethyl ester (2.91 g, 7.5 mmol) in THF (25 ml) and the mixture was stirred at RT for approx. 18 h. The mixture was concentrated i. vac. and water was added to the residue. The alkaline residue was extracted with MC (2×50 ml). The aqueous phase was adjusted to pH 1-2 with conc. hydrochloric acid and extracted with EtOAc (3×30 ml). These combined organic phases were dried with Na2SO4 and concentrated i. vac. Toluene was repeatedly added to the residue and the mixture concentrated i. vac. Yield: 1.77 g (65%)

Workup

  1. concentrationThe mixture was concentrated i
  2. additionand water was added to the residue
  3. extractionThe alkaline residue was extracted with MC (2×50 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThese combined organic phases were dried with Na2SO4
  6. concentrationconcentrated i
  7. additionToluene was repeatedly added to the residue
  8. concentrationthe mixture concentrated i

Sources & evidence

ORD record
ord-e8bfc7f0a53d45e2a0e92ba0e9f17195
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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