Ethyl Acetate → HCID 54351681, compound

HRID 2288009Notes

Reaction equation

HRID 2288009 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:15])=[O:16])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)2×HCID 53758783HCID 53758783, compound

Product 1

HCID 54351681HCID 54351681, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 10 g (26.3 mmol) of N-[[4-(phenylthio)phenyl]sulfonyl]glycine, 1,1-dimethylethyl ester from Example 6a in 50 mL of anhydrous dimethylformamide, was added 9.80 g (52.7 mmol) of 4-(2-chloroethyl)morpholine hydrochloride, followed by 10.9 g (79.0 mmol) of powdered potassium carbonate. The mixture was heated to 50° C. with vigorous stirring and maintained there for 20 hours. A sample was removed and analyzed by HPLC and shown to contain starting material, whereupon 4.90 g (26.3 mmol) of 4-(2-chloroethyl)morpholine hydrochloride, followed by 3.63 g (26.3 mmol) of powdered potassium carbonate was added and heating continued for an additional 4 hours at 70° C. The solution was cooled, ethyl acetate and water added, the organic layer separated and washed 4 times with brine, dried with sodium sulfate, filtered and concentrated to afford crude product. This was chromatographed on silica gel using 0-5% methanol/ethyl acetate to yield 12.9 g of pure N-[[4-(phenylthio)phenyl]sulfonyl]-N-[2-(4-morpholinyl)ethyl]glycine, 1,1-dimethylethyl ester, m/e=490 (M+H).

Workup

  1. temperaturemaintained there for 20 hours
  2. customA sample was removed
  3. additionwas added
  4. temperatureheating
  5. temperatureThe solution was cooled
  6. customthe organic layer separated
  7. washwashed 4 times with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford crude product
  12. customThis was chromatographed on silica gel using 0-5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-cb90a1f3185643909a87a2a37891d34a
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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