Water → HCID 53891699, compound

HRID 2288004Notes

Reaction equation

HRID 2288004 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N:29]1([CH2:28][CH2:27][N:18]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:10][CH:11]=2)(=[O:17])=[O:16])[C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 53699891HCID 53699891, compound

Product 1

HCID 53891699HCID 53891699, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, methyl ester from Example 4b (6.4 g, 17.5 mmol), 4-(2-chloroethyl)morpholine hydrochloride (9.77 g, 52.5 mmol), and potassium carbonate (10 g, 72.4 mmol) in dry DMF (60 mL) was heated to 70° C. for 16 hours. After cooling to room temperature, mixture was poured into water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, dried over MgSO4, and concentrated to afford an oil which was purified by chromatography (40/100 acetone/hexane) to give N-[2-(4-morpholinyl)ethyl]-N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, methyl ester, (6.86 g, 81.86%) as an oil. The proton NMR was consistent with N-[2-(4-morpholinyl)ethyl]-N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, methyl ester. HR mass calculated for C23H30N2O5S2 : 478.1597.Found: 478.1596.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto afford an oil which
  7. customwas purified by chromatography (40/100 acetone/hexane)

Sources & evidence

ORD record
ord-9cccf4865113479694d1c89d21d104f7
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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