4-Chlorobenzenesulfonyl chloride → HCID 10413590, compound

HRID 465572Notes

Reaction equation

HRID 465572 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-thiaoctanoate in 1.5 ml methylene chloride is added a few crystals of 4-dimethylaminopyridine followed by 60 mcl triethylamine and 0.068 g p-chlorophenylsulfonyl chloride. The mixture is stirred at room temperature for 18 h, 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-b9725b45e3fc4deba2556e3bea9a9f5f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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