Aziridine → HCID 9863629, compound

HRID 1058509Notes

Reaction equation

HRID 1058509 reaction equation
Cl[C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:6]([CH:15]=1)[C:7]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])=[O:8].[NH:23]1[CH2:25][CH2:24]1>CCOC(C)=O>[N:23]1([C:2]2[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:6]([CH:15]=2)[C:7]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])=[O:8])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 11268205HCID 11268205, compound

Product 1

HCID 9863629HCID 9863629, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the above benzamide (0.84 g, 2.38 mmol) and aziridine (0 74 mL, 14 3 mmol) in EtOAc (20 mL) was stirred at room temperature for 16 h. The reaction mixture was worked up and the residue was chromatographed on silica gel, eluting with EtOAc/MeOH (4:1) to give 10 (0.65 g, 76%), mp (EtOAc) 120-123° C. 1H NMR [(CD3)2SO] δ8.71 (t, J=5.8 Hz, 1H, NH), 8.45 (s, 1H, H-3), 744 (s, 1H, H-6), 477 (d, J=5 0 Hz, 1H, CHOH), 4.54 (t, J=5 8 Hz, 1H, CH2OH), 3.70-361 (m, 1H, CHOH), 3.45-3.36 (m, 3H, CH2OH, CONHCHH), 3 41 (s, 3H, CH3), 3.17-3.07 (m, 1H, CONHCHH), 2.47 (s, 4H, aziridine-H). Anal. Calcd for C13H17N3O7S.0.5H2O: C, 42.39,H, 4.93; N, 11.41. Found C, 41.98; H, 5.11, N, 10.97%.

Workup

  1. customthe residue was chromatographed on silica gel
  2. washeluting with EtOAc/MeOH (4:1)

Sources & evidence

ORD record
ord-0198578dd9a64ed4b0671b4034e20eef
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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