Triethylamine → HCID 53786533, compound

HRID 962735Notes

Reaction equation

HRID 962735 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[C:22]([OH:24])=O)(=[O:15])=[O:14].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[O:14]=[S:13]1(=[O:15])[C:16]2=[CH:17][N:18]=[CH:19][CH:20]=[C:21]2[C:22](=[O:24])[N:12]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 54164825HCID 54164825, compound

Product 1

HCID 53786533HCID 53786533, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 19 g of N-(4-(2-tetrahydropyranyloxy)butyl) 4-carboxypyridine-3-sulfonamide and 16 mL of triethylamine in 300 mL of dichloromethane at 0° C. was added 6.5 mL of methyl chloroformnate dropwise. After 30 min, the mixture was shaken with 100 mL of saturated sodium bicarbonate, dried over MgSO4 and concentrated under reduced pressure. Chromatography of the dark brown oil over silica gel, eluting with 1:1 ethyl acetate:hexane gave 16 g of homogeneous 1,1-dioxido-2-(4-(2-tetrahydropyranyloxy) butyl)-isothiazolo[5,4-c]pyridin-3(2H)-one as an amber oil.

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated under reduced pressure
  3. washChromatography of the dark brown oil over silica gel, eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-6e3ee62791e8412083cda73d051fa492
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

Loading…