Dimethylformamide → HCID 9801653, compound

HRID 842239Notes

Reaction equation

HRID 842239 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11]([S:14]([CH:17]([CH2:22][CH3:23])C(OC)=O)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.C=NS(=O)=[O:31].C(=O)([O-])[O-].[K+].[K+].C(NC(=O)O)C.BrCCNCCBr.C[N:53](C)[CH:54]=[O:55]>>[OH:31][NH:53][C:54](=[O:55])[CH:17]([S:14]([N:11]1[CH2:12][CH2:13][CH:8]([O:7][C:6]2[CH:24]=[CH:25][C:3]([C:2]([F:26])([F:27])[F:1])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15])[CH2:22][CH3:23]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 22052595HCID 22052595, compoundHCID 86596750HCID 86596750, compoundHCID 178486263HCID 178486263, compound

Product 1

HCID 9801653HCID 9801653, compoundYield 10%

Conditions

Temperature
60 °C

Procedure

Part F: Preparation of methyl 2-[[4-[4-(trifluoromethyl)phenoxy]-1-piperidinyl]-sulfonyl]butanoate. To a solution of the methylene sulfonamide from Part E (6.15 g, 16 mmol) in dimethylformamide (32 mL) were added potassium carbonate (7.8 g, 56.6 mmol), bis-(2-bromoethyl)amine ethyl carbamate (3.0 g, 10.75 mmol; partially purified) and 18-Crown-6 (500 mg). The resulting slurry was stirred at 60° C. After sixteen hr, potassium carbonate (2.0 g, 14 mmol) was added and the reaction stirred at 60° C. After a total of twenty four hr, the reaction was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water three times, brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) provided the ethyl sulfonamide as a light yellow oil (0.3 g, 10%).

Workup

  1. custompartially purified) and 18-Crown-6 (500 mg)
  2. waitAfter sixteen hr
  3. stirringthe reaction stirred at 60° C
  4. concentrationAfter a total of twenty four hr, the reaction was concentrated in vacuo
  5. washwashed with water three times, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27ff59cc9bda4e1da59ba42967bfe507
Source dataset
uspto-grants-2002_04
Patent number
US06372758B1

Reaction notes

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