4-Chlorobenzenesulfonyl chloride → HCID 10323499, compound

HRID 1494107Notes

Reaction equation

HRID 1494107 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×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.34 g methyl 8-amino-2,2-di-methyl-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° C.; 0.208 g (0.96 mmol) p-chlorobenzenesulfonyl chloride is added, the reaction is allowed to warm to room temperature and stirred for 48 hours. 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. temperatureto warm to room temperature
  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-071158562c68465b8ae898933ca2c1e9
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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