4-Chlorobenzenesulfonyl chloride → HCID 10413590, compound

HRID 1494114Notes

Reaction equation

HRID 1494114 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOCC>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10087643HCID 10087643, compound

Product 1

HCID 10413590HCID 10413590, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.219 g ethyl 8-amino-4-[3-(3-pyridyl)propyl]-3-thia-octanoate in 1.5 mL methylene chloride is added a few crystals of 4-dimethylaminopyridine followed by 60 mcL triethylamine and 0.068 g p-chlorobenzenesulfonyl chloride. The mixture is stirred at room temperature for 18 hours, diluted with ether and washed with saturated aqueous sodium bicarbonate. The ether layer is dried, filtered and evaporated to leave an amber oil which is chromatographed using 3:2 ethyl acetate, hexane to give ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-3-thia-octanoate as an oil; NMR (CDCl3): delta 8.0 (d,2H), 7.55 (d,2H), 3.15 (s,2H); such being the compound of formula X wherein X represents sulfur, Ar represents p-chlorophenyl, Het represents 3-pyridyl and R1 represents ethoxy.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialThe ether layer is dried
  3. filtrationfiltered
  4. customevaporated
  5. customto leave an amber oil which
  6. customis chromatographed

Sources & evidence

ORD record
ord-516ae1195fb84ff689a9c4183bc2caef
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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