Potassium Carbonate → HCID 66714132, compound

HRID 2173760Notes

Reaction equation

HRID 2173760 reaction equation
CS([O:5][CH2:6][CH2:7][N:8]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])(=[O:20])=[O:19])[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=O)=O.C([O-])([O-])=O.[K+].[K+].O[C:37]1[CH:42]=[C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[N:40]=[C:39]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH:38]=1>CN(C=O)C>[C:14]([O:13][C:11]([CH2:10][CH2:9][N:8]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])(=[O:20])=[O:19])[CH2:7][CH2:6][O:5][C:37]1[CH:38]=[C:39]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[N:40]=[C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:42]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87121174HCID 87121174, compoundHCID 178469316HCID 178469316, compound

Product 1

HCID 66714132HCID 66714132, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 10.6 g of tert-butyl 3-[(2-methanesulfonyloxy-ethyl)-(2-nitro-benzenesulfonyl)-amino]-propionate in 220 ml of DMF was added 16.2 g of K2CO3 and 5.6 g of diethyl 4-hydroxy-pyridine-2,6-dicarboxylate. The mixture was heated for 20 hours at 60° C. and then concentrated under reduced pressure and taken up in 200 ml of water and 200 ml of EtOAc. The aqueous phase was extracted 2× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4, concentrated under reduced pressure and purified by flash chromatography on silica (Merck EasyVarioPrep 600 g column, Si60 15-40 μm), using a gradient of 0 to 20% EtOAc in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 6.56 g of diethyl 4-{2-[(2-tert-butoxycarbonyl-ethyl)-(2-nitro-benzenesulfonyl)-amino]-ethoxy}-pyridine-2,6-dicarboxylate were obtained. LC/MS (C): tr=4.14 min; [M+H]+: m/z 596.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe aqueous phase was extracted 2× with EtOAc
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash chromatography on silica (Merck EasyVarioPrep 600 g column, Si60 15-40 μm)
  7. additionThe fractions containing the desired product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c187d0fcda0f42b085f9f00d12f64588
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

Loading…