4-Toluenesulfonyl chloride → Sarcosine, N-(p-tolylsulfonyl)-, ethyl ester

HRID 1597422Notes

Reaction equation

HRID 1597422 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])[CH3:3].C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:8][N:7]([S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 95252Sarcosine, N-(p-tolylsulfonyl)-, ethyl esterYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold suspension of sarcosine ethyl ester hydrochloride salt (3.1 g, 20 mmol) in CH2Cl2 (150 mL) was sequentially treated with triethyl amine (4.45 g, 44 mmol) and tosyl chloride (4.19 g, 22 mmol) and stirred for 1 h, after which time the ice bath was removed, and the reaction was allowed to stir for an additional 1 h. The reaction mixture was then partitioned between water and CH2Cl2 and the organic extract was washed with brine, dried, filtered, and concentrated to give 5.7 g of the title compound as a white solid.

Workup

  1. customafter which time the ice bath was removed
  2. stirringto stir for an additional 1 h
  3. customThe reaction mixture was then partitioned between water and CH2Cl2
  4. extractionthe organic extract
  5. washwas washed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a38014214b0e4c1cac65ae841d2b9373
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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