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1-Propanesulfonyl chloride → HCID 22176535, compound

HRID 1797203
Notes
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Reaction equation

HRID 1797203 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][CH3:20])=[CH:15][CH:14]=1)([OH:12])[CH3:11].[CH2:21]1CCN2C(=NCCC2)CC1>C1COCC1>[OH:12][C:10]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)([CH3:11])[CH2:9][NH:8][S:4]([CH:1]([CH3:2])[CH3:21])(=[O:5])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 170393691-Amino-2-(4-methoxyphenyl)propan-2-ol

Product 1

HCID 22176535HCID 22176535, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL-3n flask fitted with a stirrer and thermometer, 2.53 g. of propanesulfonyl chloride was added dropwise to 3.00 g. of 1-amino-2-(4-methoxyphenyl)propan-2-ol and 2.70 g. of DBU in THF (200 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 3.61 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 (2.71 g, 57%) as a white solid. Ion spray M.S. 286.2 (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 3.61 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-2007b37ba85e4b1c8e041e2591bdd8a1
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07034045B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes