Potassium Carbonate → HCID 60679428, compound

HRID 2288007Notes

Reaction equation

HRID 2288007 reaction equation
C1(SC2C=CC(S([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=O)=O)=CC=2)CCCCC1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.CN(C)C(=O)C>O>[N:35]1([CH2:34][CH2:33][NH:17][CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 767274-(2-Chloroethyl)morpholineHCID 54562908HCID 54562908, compound

Product 1

HCID 60679428HCID 60679428, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The N-[[4-(cyclohexylthio)phenyl]sulfonyl]glycine, 1,1-dimethylethyl ester, from Example 5b (3.34 mmol, 1.145 g), dried 325 mesh K2CO3 (13.4 mmol, 1.84 g), N-(chloroethyl)morpholine (10 mmol, 1.86 g), and N,N-dimethyacetamide (13 mL) were combined and heated at 60° C. under an inert atmosphere for 16 hours, then an additional 4 hours at 80° C. Water (40 mL) was added, and the mixture was extracted with ethyl acetate (100 mL, then 50 mL). The combined organic phases were dried (MgSO4), filtered through a silica plug, concentrated, and subjected to chromatography (ethyl acetate:toluene 1:1), to afford N-[[4-(cyclohexylthio)phenyl]phenyl]sulphonyl]-N-[2-(4-morpholinyl)ethyl]-glycine, 1,1-dimethylethyl ester (954 mg, 57%) as an oil. The structure was verified spectroscopically. MS MH+ calcd. for C24H38N2O5S2 : 499, found: 499. Elemental anal. calc'd for C24H38N2O5S2.0.25H2O: C, 57.29; H, 7.71; N, 5.57. Found: C, 57.32; H, 8.21; N, 5.27.

Workup

  1. customan additional 4 hours
  2. customat 80° C
  3. extractionthe mixture was extracted with ethyl acetate (100 mL
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered through a silica plug
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc87da291b39428da0857a354bc74b58
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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