4-Toluenesulfonyl chloride → HCID 19848776, compound

HRID 1607460Notes

Reaction equation

HRID 1607460 reaction equation
C[O:2]C1C=C(CNCCCNCCCCNCCCN)C=CC=1O.O[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]([CH3:44])([CH3:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:34]=2)[CH2:29][CH:28]([CH2:45][CH2:46][NH2:47])[C:27]1([CH3:49])[CH3:48].C(N(CC)CC)C.[C:57]1([CH3:67])[CH:62]=[CH:61][C:60]([S:63](Cl)(=[O:65])=[O:64])=[CH:59][CH:58]=1>C(Cl)Cl>[OH:2][C:31]1[CH:32]=[C:33]([C:36]([CH3:44])([CH3:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:34]=[C:35]2[C:30]=1[CH2:29][CH:28]([CH2:45][CH2:46][NH:47][S:63]([C:60]1[CH:61]=[CH:62][C:57]([CH3:67])=[CH:58][CH:59]=1)(=[O:65])=[O:64])[C:27]([CH3:49])([CH3:48])[NH:26]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 131714023HCID 131714023, compound

Product 1

HCID 19848776HCID 19848776, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To 20 ml of methylene,chloride is added 346 mg (1 mmole) dl-5-hydroxy-3-[2-aminoethyl)-7-(1,1-dimethylheptyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline and 0.166 ml (1.2 mmole) triethylamine. The solution is cooled to -20° C. and a solution of 191 mg (1 mmole) p-toluenesulfonyl chloride in 10 ml methylene chloride is added dropwise over ten minutes. The mixture is allowed to warm to 0° C., poured into ice/water and the layers separated. The aqueous layer is extracted with fresh methylene chloride, the combined organic layers washed with water, saturated sodium bicarbonate solution, brine and dried over anhydrous magnesium sulfate. Evaporation of solvent affords the crude product which is purified by chromatograpy on silica gel. In like manner the remaining amines provided in Example 66 are reacted with sulfonyl chlorides of the formula R17SO2Cl to provide compounds of the formula ##STR95## where f, R2 -R5, M, Z and W are as defined in Example 66 and R17 is as defined below.

Workup

  1. temperatureto warm to 0° C.
  2. customthe layers separated
  3. extractionThe aqueous layer is extracted with fresh methylene chloride
  4. washthe combined organic layers washed with water, saturated sodium bicarbonate solution, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-47ddfcc57d7a4bc5a7041560db395338
Source dataset
uspto-grants-1989_09
Patent number
US04863934

Reaction notes

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