Potassium Carbonate → methyl N-[(6-chloropyridin-3-yl)sulfonyl]-N-cyclopentylglycinate

HRID 45248Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2 g (7.67 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 0.7 mL (7.67 mmol) of methyl bromoacetate and 1.2 g (8.4 mmol) of K2CO3 in 15 mL of CH3CN is heated for 12 hours at 80° C. After cooling to room temperature, the medium is filtered and the filtrate is concentrated. The residue is taken up in 100 mL of DCM, washed successively with 50 mL of saturated NaHCO3 solution and 50 mL of water, and the organic phase is then dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with an 8/2 heptane/EtOAc mixture. 2.4 g of methyl N-[(6-chloropyridin-3-yl)sulfonyl]-N-cyclopentylglycinate are obtained in the form of an oil.

Workup

temperatureAfter cooling to room temperature
filtrationthe medium is filtered
concentrationthe filtrate is concentrated
washwashed successively with 50 mL of saturated NaHCO3 solution and 50 mL of water
dry with materialthe organic phase is then dried over Na2SO4
concentrationconcentrated under reduced pressure
custompurified by chromatography on a column of silica gel
washeluting with an 8/2 heptane/EtOAc mixture

Sources & evidence

ORD record: ord-714d01a295904cbcb2891931551fc56b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541455B2

Reaction notes

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