Triethylamine → HCID 14986692, compound

HRID 465597Notes

Reaction equation

HRID 465597 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.[F:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:14]=2)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:41])=[O:40])=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 14986691HCID 14986691, compound

Product 1

HCID 14986692HCID 14986692, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.144 g (0.44 mmol) methyl 8-amino-4-[m-(3-pyridyl)-phenyl]-octanoate in 2 ml methylene chloride is added a catalytic amount (0.02 g) 4-dimethylaminopyridine followed by 0.08 ml (0.57 mmol) triethylamine and 0.098 g (0.5 mmol) p-fluorophenylsulfonyl chloride. The mixture is stirred at room temperature for 18 h, diluted with methylene chloride, washed with saturated sodium bicarbonate solution, water and brine, dried, filtered and evaporated to give a greenish oil which is purified by chromatography using 3:2 ethyl acetate/hexane as eluent to obtain methyl 8-(p-fluorophenylsulfonamido)-4-[m-(3-pyridyl)-phenyl]-octanoate as an oil; NMR (CDCl3): delta 3.63 (s,3H), 2.9 (q,2H), 8.95 (d,1H), 8.67 (dd,2H).

Workup

  1. washwashed with saturated sodium bicarbonate solution, water and brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customto give a greenish oil which
  6. customis purified by chromatography

Sources & evidence

ORD record
ord-82b4fe1c4780481e811d40afc292ebb2
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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