4-Toluenesulfonyl chloride → HCID 53845555, compound

HRID 465648Notes

Reaction equation

HRID 465648 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:13]([C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[C:17]=1[NH2:18])([CH3:15])[CH3:14].C(N(CC)CC)C.[S:33](Cl)([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34]>ClCCl>[CH3:24][CH:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:16]([CH:13]([CH3:15])[CH3:14])[C:17]=1[NH:18][C:10](=[O:12])[C@@H:2]([NH:1][S:33]([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:25]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18648024HCID 18648024, compound

Product 1

HCID 53845555HCID 53845555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.61 g (1.88 mmol) (2,6-diisopropylaniline)-L-phenylalanine and 0.3 mL triethylamine in 20 mL dichloromethane at 0° C. was added 0.38 g (2.0 mmol) tosyl chloride. After 30 minutes the cool bath was removed and the reaction was stirred for 16 hours. The reaction mixture was taken up in dichloromethane and washed successively with dilute aqueous citric acid and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Obtained was a white powder that was recrystallized from diethyl ether. Yield: 0.75 g, mp 183°-184° C.

Workup

  1. customAfter 30 minutes the cool bath was removed
  2. washwashed successively with dilute aqueous citric acid and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customObtained
  7. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-2c7a926569ef42dd84770854efae0b77
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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