Morpholine → HCID 72188990, compound

HRID 1487072Notes

Reaction equation

HRID 1487072 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][O:20]2)=[C:15]([OH:22])[CH:14]=1)(=[O:12])=[O:11].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:21][OH:20])=[C:15]([OH:22])[CH:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 89876041HCID 89876041, compound

Product 1

HCID 72188990HCID 72188990, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide (60 mg, 0.160 mmol) in ethanol (1 mL) at 25° C. was added morpholine (30.6 mg, 0.352 mmol) and the reaction mixture stirring at 50° C. for 12 hours. The reaction mixture was then concentrated in vacuo and purified by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated under a stream of nitrogen to give a single regioisomer of the desired product, 11.2 mg. LCMS [LCMS2] Rt 1.25 min, m/z (ES+) 463 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by mass
  3. concentrationThe relevant fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-6f560759f1004206ae8576fb71bf1828
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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