Water → HCID 69415727, compound

HRID 1351311Notes

Reaction equation

HRID 1351311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH2:9][N:10]([CH3:23])[S:11]([C:14]2[CH:18]=[C:17]([C:19](=[O:21])[CH3:20])[S:16][C:15]=2[NH2:22])(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:35])[CH2:33][CH3:34].O>O1CCCC1>[C:19]([C:17]1[S:16][C:15]([NH:22][C:32](=[O:35])[CH2:33][CH3:34])=[C:14]([S:11](=[O:13])(=[O:12])[N:10]([CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[OH:24])[CH3:23])[CH:18]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 62324Propionyl chloride2×HCID 86600997HCID 86600997, compound

Product 1

HCID 69415727HCID 69415727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-acetyl-2-amino-thiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide (the compound of Preparation Example 99) (150 mg) and triethylamine (557 μL) in tetrahydrofuran was added propionic acid chloride (195 μL) in small amounts. After stirring at room temperature for 2 hours, triethylamine (557 μL) and propionic acid chloride (195 μL) were further added, and the solution was stirred for 30 minutes. Water was added to the reaction solution, the solution was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. The residue resulting from the removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (75 mg) was obtained as a colorless solid.

Workup

  1. stirringthe solution was stirred for 30 minutes
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  4. customThe residue resulting from the removal of the solvent by evaporation
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4f94f8a7d4774097a2fa846a839c6d33
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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