Potassium Carbonate → Ethyl 4-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-butanoate

HRID 2173751Notes

Reaction equation

HRID 2173751 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])(=[O:15])=[O:14])[CH:6]=[C:5]([CH2:25][OH:26])[N:4]=1.Br[CH:28]([CH3:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:26][CH2:25][C:5]1[CH:6]=[C:7]([O:9][CH2:10][CH2:11][N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])(=[O:14])=[O:15])[CH2:35][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:8]=[C:3]([CH2:2][OH:1])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95424Butanoic acid, 3-bromo-, ethyl esterHCID 66713939N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide

Product 1

HCID 66714046Ethyl 4-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-butanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 767 mg of N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide in 15 ml of DMF, under argon, was added 344 μl of ethyl 3-bromo-butyrate and 1.38 g of K2CO3. The mixture was stirred for about 20 hours at 40° C. and then filtered through a sinter of porosity 4. The cake was washed with EtOAc and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica (Merck SuperVarioPrep 90 g column, Si60 15-40 μm), using a gradient of 0 to 10% MeOH in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 395 mg of ethyl 4-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-butanoate were obtained. LC/MS (B): tr=2.72 min; [M+H]+: m/z 498; [M+HCO2H−H]−: m/z 542.

Workup

  1. filtrationfiltered through a sinter of porosity 4
  2. washThe cake was washed with EtOAc
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography on silica (Merck SuperVarioPrep 90 g column, Si60 15-40 μm)
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f5c4727f4ca421ca3be096bffd4db50
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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