Aziridine → HCID 11186420, compound

HRID 1058516Notes

Reaction equation

HRID 1058516 reaction equation
Cl[C:2]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([OH:11])[CH2:9][OH:10])=[O:5].[NH:22]1[CH2:24][CH2:23]1>CCOC(C)=O>[N:22]1([C:2]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:3]=2[C:4]([NH:6][CH2:7][CH:8]([OH:11])[CH2:9][OH:10])=[O:5])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 10543652HCID 10543652, compound

Product 1

HCID 11186420HCID 11186420, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-chloro-N-(2,3-dihydroxypropyl)-3,5-dinitrobenzamide (Palmer et al., J. Med. Chem. 1996, 39, 2518-2528) (670 mg, 2.10 mmol) in EtOAc (35 mL) was treated with aziridine (325 μL, 6 28 mmol) at room temperature for 3 h, then concentrated under reduced pressure. The residue was dissolved in warm EtOAc (220 mL) and filtered though a short column of silica gel to give 17 (304 mg, 44%). mp (EtOAc/petroleum ether) 154-155° C., 1NMR [(CD3)2SO] δ8.74 (d, J=2.7 Hz, 1H, H-4), 8.57 (t, J=5 6 Hz, 1H, NH), 8.36 (d, J=2.7 Hz, 1 H, H-6), 4 88 (d, J=5.3 Hz, 1H, CHOH), 4.64 (t, J=5.7 Hz, 1H, CH2OH), 3 73-3 63 (m, 1H, CHOH), 3.52-3.42 (m, 1H, NHCHH), 3.42-3.34 (m, 2H, CH2OH), 3.26-3.15 (m, 1H, NHCHH), 2.39 (s, 4H, aziridine-H). Anal. Calcd for C12H14N4O7. C, 44.2;H, 4.3, N, 17.2. Found: C, 44.3;H, 4.2, N, 17.3%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in warm EtOAc (220 mL)
  3. filtrationfiltered though a short column of silica gel

Sources & evidence

ORD record
ord-86df1c3ce592440d8e3a0e472f6de958
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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