4-Toluenesulfonyl chloride → HCID 87946725, compound

HRID 1835874Notes

Reaction equation

HRID 1835874 reaction equation
[CH2:1]([O:5][C:6]([N:8]([S:45]([C:48]1[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=1)(=[O:47])=[O:46])[CH2:9][CH2:10][N:11]([S:35]([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:12][CH2:13][N:14]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[O:7])[CH2:2][CH2:3][CH3:4].CCN(CC)CC.[C:62]1([CH3:72])[CH:67]=[CH:66][C:65]([S:68](Cl)(=[O:70])=[O:69])=[CH:64][CH:63]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[S:68]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:14]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:13][CH2:12][N:11]([S:35]([C:38]1[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][CH:43]=1)(=[O:36])=[O:37])[CH2:10][CH2:9][N:8]([C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[S:45]([C:48]1[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=1)(=[O:46])=[O:47])([C:65]1[CH:66]=[CH:67][C:62]([CH3:72])=[CH:63][CH:64]=1)(=[O:70])=[O:69]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 8471TriethylamineHCID 23500250HCID 23500250, compound

Product 1

HCID 87946725HCID 87946725, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 5.47 g of 16-butoxycarbonyl-10, 13,16-tri(p-toluenesulfonyl)-10, 13,16-triazahexadecanol in 200 ml of CH2Cl2, 2.95 g of Et3N was added and the mixture was cooled to 0° C. To the well stirred solution was added dropwise at 0° C. 0.22 g of 4-dimethylaminopyridine and then 1.67 g of p-toluenesulfonyl chloride in 100 ml of CH2Cl2 was added. The reaction was continued overnight at room temperature. A 0.04 g amount of 4-dimethylaminopyridine and 0.33 g of p-toluenesulfonyl chloride were added at 7° C. and stirring was continued for 4 hours. The mixture was extracted with water twice. The organic layers were dried over MgSO4, filtered and evaporated under reduced pressure and eluted with CH2Cl2 and CH2Cl2/ethyl acetate (100/1 v/v). About 4.21 g of product was obtained. The preparation scheme is shown below:

Workup

  1. additionwas added dropwise at 0° C
  2. stirringstirring
  3. waitwas continued for 4 hours
  4. extractionThe mixture was extracted with water twice
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. washeluted with CH2Cl2 and CH2Cl2/ethyl acetate (100/1 v/v)

Sources & evidence

ORD record
ord-0eda0df9bcb84c0494e240a317b11248
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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