Triethylamine → HCID 9795374, compound

HRID 1250551Notes

Reaction equation

HRID 1250551 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[C:16]1([CH2:22][S:23](Cl)(=[O:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.O>[C:16]1([CH2:22][S:23]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([NH2:5])=[O:4])(=[O:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 111306L-Prolinamide

Product 1

HCID 9795374HCID 9795374, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of L-prolinamide (2.28 g, 20 mmol) and triethylamine (5.76 ml, 42 mmol) in 40 ml methylene chloride was added 3.92 g (20 mmol) α-toluenesulfonyl chloride at 0° C. with stirring. The reaction was gradually warmed up to room temperature and stirred overnight. The mixture was diluted with water, and extracted into 200 ml methylene chloride. The organic extract was concentrated and further purified by silica gel to give 3.0 g product as a white solid (55.7% yield). 1H NMR (CDCl3): d 01.89 (m, 3H); 2.25 (m, 1H); 3.40 (m, 1H); 3.50 (m, 1H); 3.96 (m, 1H); 4.35 (s, 2H); 7.39-7.45 (m, 5H, aromatic).

Workup

  1. stirringstirred overnight
  2. extractionextracted into 200 ml methylene chloride
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. customfurther purified by silica gel

Sources & evidence

ORD record
ord-9efc471581be45149370d716dfd5ff22
Source dataset
uspto-grants-2002_01
Patent number
US06339101B1

Reaction notes

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