Water → HCID 22176531, compound

HRID 1797194Notes

Reaction equation

HRID 1797194 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:27])([CH3:26])[CH2:18][NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[CH:13][CH:12]=1.C(N(CC)CC)C.O>C1COCC1>[OH:27][C:17]([C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)([CH3:26])[CH2:18][NH:19][S:20]([CH:23]([CH3:24])[CH3:25])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22176564HCID 22176564, compound

Product 1

HCID 22176531HCID 22176531, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100 mL single-neck flask, 77 mg of benzoyl chloride was added dropwise to 135 mg of [2-(4-aminophenyl)-2-hydroxypropyl][(methylethyl)sulfonyl]amine and 56 mg of triethylamine in THF (20 mL) while stirring under a nitrogen atmosphere at room temperature. The reaction was allowed to stir at this temperature for 2 h. The mixture was then poured into H2O and the desired product was extracted into ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 233 mg as a solid. This material was purified via silica gel chromatography employing the Chromatotron, using a 2000 micron rotor and eluting with a solvent of ethyl acetate to yield the intermediate title compound (151 mg, 80%) as a white solid. Ion spray M.S. 375.2 (M*−1).

Workup

  1. stirringto stir at this temperature for 2 h
  2. extractionthe desired product was extracted into ethyl acetate
  3. dry with materialdried over K2CO3
  4. concentrationconcentrated under reduced vacuum
  5. customto yield 233 mg as a solid
  6. customThis material was purified via silica gel chromatography
  7. washeluting with a solvent of ethyl acetate

Sources & evidence

ORD record
ord-8409b67a845d4554a8ba89c0720409ea
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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