3-Amino-3-methyloxetane → HCID 89876232, compound

HRID 1487069Notes

Reaction equation

HRID 1487069 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)=[CH:15][C:14]=1[CH3:22])(=[O:12])=[O:11].[CH3:27][C:28]1([NH2:32])[CH2:31][O:30][CH2:29]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]([OH:20])[CH2:21][NH:32][C:28]2([CH3:27])[CH2:31][O:30][CH2:29]2)=[CH:15][C:14]=1[CH3:22])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 468357253-Amino-3-methyloxetane2×HCID 89875886HCID 89875886, compound

Product 1

HCID 89876232HCID 89876232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-(2,4-dimethylphenyl)-N-isobutyl-2-methyl-4-(oxiran-2-yl)benzenesulfonamide (20 mg, 0.054 mmol) in ethanol at 25° C. was added 3-methyloxetan-3-amine (5.08 mg, 0.058 mmol). The reaction mixture was then stirred at 50° C. for 18 hours. Another portion of 3-methyloxetan-3-amine (5.08 mg, 0.058 mmol) was then added and the reaction stirred for a further 8 hours at 50° C. The reaction mixture was concentrated in vacuo and purified by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated under a stream of nitrogen to give the required product, 5.2 mg. LCMS [LCMS2] Rt 1.23 min, m/z (ES+) 461 (M+H).

Workup

  1. stirringthe reaction stirred for a further 8 hours at 50° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by mass
  4. concentrationThe relevant fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-d3f52add35b14677939ecda9344334ee
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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