4-Chlorobenzenesulfonyl chloride → HCID 10323499, compound

HRID 465562Notes

Reaction equation

HRID 465562 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10041705HCID 10041705, compound

Product 1

HCID 10323499HCID 10323499, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.34 g methyl 8-amino-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate in 5 ml dry methylene chloride is added a catalytic amount of 4-dimethylaminopyridine followed by 0.2 ml triethylamine and the mixture is cooled to 0°; 0.208 g (0.96 mmol) p-chlorophenylsulfonyl chloride is added, the reaction mixture is allowed to warm to room temperature and stirred for 48 h. The mixture is diluted with methylene chloride and washed with saturated sodium bicarbonate, water and brine. The organic phase is dried, filtered and evaporated to yield an amber oil which is purified by flash chromatography using 1:1 ethyl acetate/hexane to yield methyl 8-(p-chlorophenylsulfonamido)-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate; IR (CH2Cl2): 3381, 1729, 1164 cm-1 ; NMR (CDCl3): delta 3.57 (s,3H), 2.9 (q,2H), 2.53 (t,2H), 1.12 (s,6H).

Workup

  1. temperaturethe mixture is cooled to 0°
  2. washwashed with saturated sodium bicarbonate, water and brine
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customto yield an amber oil which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-22ace18e4c8b4d7aa97e3584be5fdf1a
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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