Tert-Butyl hypochlorite → HCID 54581543, compound

HRID 1770735Notes

Reaction equation

HRID 1770735 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6]([CH3:12])([CH3:11])[C:5]1=[O:13].C(O[Cl:19])(C)(C)C>CO>[Cl:19][N:7]1[C:8](=[O:10])[CH2:9][N:4]([CH2:3][CH2:2][OH:1])[C:5](=[O:13])[C:6]1([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 199580901-(2-Hydroxyethyl)-3,3-dimethylpiperazine-2,5-dione

Product 1

HCID 54581543HCID 54581543, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-hydroxyethyl)-3,3-dimethylpiperazine-2,5-dione (300 mg, 1.61 mmol) in methanol (3 ml) was cooled to 0° C. tert-Butylhypochlorite (272 ul, 2.4 mmol) was added. The resulting solution was stirred for 35 minutes, and then concentrated under reduced pressure. The crude material was purified by column chromatography, eluting the desired product from silica gel with a gradient of 1 to 10% methanol in dichloromethane to give the title compound as a white solid (284 mg, 1.28 mmol, 80%). 1H NMR (D2O, 400 MHz) δ 1.67 (s, 6H), 2.26-2.28 (t, J=5.0 Hz, 1H), 3.59-3.62 (t, J=5.0 Hz, 2H), 3.86-3.90 (q, J=5.0 Hz, 2H), 4.32 (s, 2H); LRMS (ESI/APCI) m/z 221 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by column chromatography
  4. washeluting the desired product from silica gel with a gradient of 1 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-7ee8ce1708d74fffb4eec9a90e98091a
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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