Propargylamine → HCID 86587113, compound

HRID 2414580Notes

Reaction equation

HRID 2414580 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([S:10]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[C:22]#[CH:23]>CN(C)C=O>[CH3:9][N:8]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([NH:24][CH2:21][C:22]#[CH:23])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 53729790HCID 53729790, compound

Product 1

HCID 86587113HCID 86587113, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1.820 g (6.00 mmol) of of [(4-fluoro-benzenesulfonyl-methyl-amino]-acetic acid tert-butylester in 25 mL of dimethylformamide was added 5.0 mL (4.0 g, 72.89 mmol) of propargylamine. The mixture was heated to 80° C. and stirred for 48 h. The mixture was partitioned between 400 mL of dichloromethane and 200 mL of 20% aqueous NH4Cl solution. The organic layer was separated, washed with 200 mL of water, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Silica gel column chromatography of the residue, eluting with 1% MeOH/CH2Cl2, provides 1.067 g (53%) of 2-(methyl{[4-(prop-2-ynylamino)phenyl]sulfonyl}-amino)acetic acid, tert-butyl ester as a light brown oil. Electrospray Mass Spec 339.3 (M+H)+

Workup

  1. customThe mixture was partitioned between 400 mL of dichloromethane and 200 mL of 20% aqueous NH4Cl solution
  2. customThe organic layer was separated
  3. washwashed with 200 mL of water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washSilica gel column chromatography of the residue, eluting with 1% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-807c271f5638491082d7a259d9ed6b11
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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