Water → HCID 11057721, compound

HRID 1244791Notes

Reaction equation

HRID 1244791 reaction equation
FC(F)(F)C(O)=O.O.[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([S:20]([N:23]([CH2:30][CH:31](OCC)[O:32]CC)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:22])=[O:21])[CH:14]=[CH:13]2.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([S:20]([N:23]([CH2:30][CH:31]=[O:32])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:22])=[O:21])[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11812307Ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)(2,2-diethoxyethyl)amino]acetate

Product 1

HCID 11057721HCID 11057721, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixed solution of trifluoroacetic acid (5 ml), chloroform (1.5 ml) and water (2.5 ml) was added a solution of the compound obtained in Step 2 (560 mg) in chloroform (1 ml) under cooling with ice water. After stirring for 1.5 hours under cooling with ice water, the reaction mixture was adjusted to pH 8 with saturated aqueous solution of sodium hydrogencarbonate and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and thereafter the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1–2:1) to obtain the title compound (240 mg).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1–2:1)

Sources & evidence

ORD record
ord-e6e2e3aecd36423bafbf74e6c67e2da7
Source dataset
uspto-grants-2006_10
Patent number
US07122662B2

Reaction notes

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