Water → HCID 131728445, compound

HRID 1172475Notes

Reaction equation

HRID 1172475 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:10]=3[S:11](=[O:14])(=[O:13])[CH2:12][C:6]=2[CH:5]=[C:4]([S:23](Cl)(=[O:25])=[O:24])[CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.O>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:10]=3[S:11](=[O:14])(=[O:13])[CH2:12][C:6]=2[CH:5]=[C:4]([S:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)(=[O:25])=[O:24])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 131728441HCID 131728441, compound

Product 1

HCID 131728445HCID 131728445, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 49j (0.2 g, 0.45mm) and morpholine (0.08 mL, 0.9 mmol) in dry ethyl acetate (25 mL) was stirred overnight at room temperature, treated with water and extracted with ethyl acetate. The organic layer was washed with 10% aqueous HCl (50 mL), water, brine, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound. Yield: 0.19 g, (86%); 1H NMR (DMSO-d6): δ 2.80 (s, 3H, CH3), 3.0 (t, 4H, 2CH2), 3.7 (s, 4H, 2CH2), 5.5 (s, 2H; CH2), 8.0 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.2 (s, 2H, Ar). MS: m/e (EI+) 487 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 10% aqueous HCl (50 mL), water, brine
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-778e1a10d3d14810a7758fec0d684552
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

Loading…