Glycine → N-((4-Methylphenyl)sulfonyl)glycine

HRID 2422923Notes

Reaction equation

HRID 2422923 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[S:6](Cl)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7]>[OH-].[Na+].C(OCC)C>[CH3:13][C:12]1[CH:14]=[CH:15][C:9]([S:6]([NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 750GlycineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 70653N-((4-Methylphenyl)sulfonyl)glycineYield 21%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Glycine (1 g, 13.32 mmol) was dissolved in 1N NaOH (aq.) and a solution of tosyl chloride (2.62 g, 13.72 mmol) in diethyl ether (15 ml) was added portion wise with stirring over 10 min. The resulting mixture was allowed to stir at room temperature for 3 h. The ethereal layer was separated and the aqueous layer treated with 2N HCl solution until acidified to pH 5. After cooling the resulting solution to 0° C., the product began to precipitate from the solution. The solid was collected by filtration and the mother liquor placed in a fridge overnight causing more of the desired product to precipitate. The solid was again collected by filtration and the combined collected solid was dried under high vacuum affording 9 as a white powder (613 mg, 21%). δH (400 MHz, MeOD) 2.41 (3H, s, CH3), 3.66 (2H, s, CH2), 7.35 (2H, d, J=8 Hz, ArH), 7.73 (2H, d, J=8 Hz, ArH); δc (100.6 MHz, MeOD) 20.3, 43.6, 127.0, 129.5, 137.6, 143.6, 171.0; MS (ES+) 246.8 (100%, [M+H2O]+); MS (ES−) 227.9 (100%, [M−H]−); HRMS [M−H]− requires 228.03360, found 228.03364.

Workup

  1. stirringto stir at room temperature for 3 h
  2. customThe ethereal layer was separated
  3. additionthe aqueous layer treated with 2N HCl solution
  4. customto precipitate from the solution
  5. filtrationThe solid was collected by filtration
  6. waitthe mother liquor placed in a fridge overnight
  7. customto precipitate
  8. filtrationThe solid was again collected by filtration
  9. customthe combined collected solid
  10. customwas dried under high vacuum

Sources & evidence

ORD record
ord-2424975df2754670b29ccdc06cb2b0c7
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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