1,2-Dichloroethane → HCID 131721867, compound

HRID 2288005Notes

Reaction equation

HRID 2288005 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][N:10]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C@@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(Cl)CCl.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[O:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]1ON>CN(C=O)C>[N:2]1([CH2:8][CH2:9][N:10]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C@@H:11]([C:13]([O:15][CH:55]2[CH2:56][CH2:57][CH2:58][CH2:59][O:54]2)=[O:14])[CH3:12])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 131721868HCID 131721868, compound

Product 1

HCID 131721867HCID 131721867, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of N-[2-(4-morpholinyl)ethyl]-N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, monohydrochloride from Example 4d (3.61 g, 7.20 mmol) in dry DMF was added EDC (2.57 g, 13.4 mmol), 4-methylmorpholine (2.96 mL, 26.96 mmol), and N-hydroxybenzotriazole (1.81 g, 13.4 mmol) at zero degrees C. After stirring for 45 minutes at zero degrees C., O-tetrahydro-2H-pyran-2-yl-hydroxylamine (1.88 g, 16.0 mmol) was added and the solution was left stirring at room temperature overnight. The reaction was concentrated and partitioned between water and ethyl acetate. The combined ethyl acetate layers were washed with water and brine, dried with MgSO4, and concentrated to a white solid (2.4 g). Chromatographic purification (40% acetone in hexane) afforded N-[2-(4-morpholinyl)ethyl]-N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, tetrahydro-2H-pyran-2-yl ester, (1.43 g, 34.6% yield) as a white solid. The proton NMR and MIR were consistent for N-[2-(4-morpholinyl)ethyl]-N-[[4-[(4-methylphenyl)thio]phenyl]sulfonyl]-D-alanine, tetrahydro-2H-pyran-2-yl ester. Anal. calc'd for C27H37N3O6S2 : C, 57.53; H, 6.62; N, 7.45; S, 11.38. Found: C, 57.43; H, 6.80; N, 7.34; S,11.34.

Workup

  1. waitthe solution was left
  2. stirringstirring at room temperature overnight
  3. concentrationThe reaction was concentrated
  4. custompartitioned between water and ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated to a white solid (2.4 g)
  8. customChromatographic purification (40% acetone in hexane)

Sources & evidence

ORD record
ord-2d9e7fb09fc64bd4952ec488a988ec65
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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