1-Propanesulfonyl chloride → HCID 22176546, compound

HRID 1797199Notes

Reaction equation

HRID 1797199 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2]C.[NH2:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)([OH:12])[CH3:11].[CH2:27]1CCN2C(=NCCC2)CC1>C1COCC1>[OH:12][C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)([CH3:11])[CH2:9][NH:8][S:4]([CH:1]([CH3:2])[CH3:27])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 150366201-Amino-2-[4-(benzyloxy)phenyl]propan-2-ol

Product 1

HCID 22176546HCID 22176546, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 1000 mL-3n flask fitted with a stirrer and thermometer, 5.69 g. of propanesulfonyl chloride was added dropwise to 8.60 g. of 1-amino-2-[4-(phenylmethoxy)phenyl]propan-2-ol and 6.21 g. of DBU in THF (300 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, reaction was concentrated under reduced vacuum. The resulting oil was taken into ethyl acetate and the organic layer was washed two times with H2O, dried over Na2SO4, and concentrated under reduced vacuum to yield 10.2 g. as a solid. This material was purified via silica gel chromatography employing the Water's prep. 2000 and eluting with a solvent of hexane/ethyl acetate 9:1 to yield intermediate title compound (6.14 g, 50%) as a white solid. Ion spray M.S. 362.2 (M*−1).

Workup

  1. customIn the morning, reaction
  2. concentrationwas concentrated under reduced vacuum
  3. washthe organic layer was washed two times with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced vacuum
  6. customto yield 10.2 g
  7. customThis material was purified via silica gel chromatography
  8. wash2000 and eluting with a solvent of hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-38dadc0dbb224853b1097612132d3a25
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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