Triethylamine → HCID 10250599, compound

HRID 1494122Notes

Reaction equation

HRID 1494122 reaction equation
[OH: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.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl.CCOCC>[CH3:30][S:31]([O: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])(=[O:33])=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10019238HCID 10019238, compound

Product 1

HCID 10250599HCID 10250599, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.094 g (0.29 mmol) ethyl 8-hydroxy-4-[3-(3-pyridyl)propyl]-3-thia-octanoate in 1.5 mL methylene chloride is cooled to 0° and then 0.1 mL of triethylamine is added followed by 0.027 mL methanesulfonyl chloride. The reaction is stirred at 0° C. for 1 hour and diluted with ether. The ether layer is washed with saturated sodium bicarbonate, water, brine, then dried, filtered and evaporated to yield ethyl 8-methanesulfonyloxy-4-[3-(3-pyridyl)propyl]-3-thia-octanoate; NMR (CDCl3): delta 3.2 (s,2H), 3.1 (s,3H).

Workup

  1. washThe ether layer is washed with saturated sodium bicarbonate, water, brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d2f703129b2241efbe6d7c87057a069f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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