Imidazole → HCID 66919892, compound

HRID 1971748Notes

Reaction equation

HRID 1971748 reaction equation
[C:1]([N:5]1[CH2:30][CH2:29][CH2:28][CH2:27][C:8]2[C:9]([Br:26])=[C:10]3[C:19]4[CH:18]=[C:17]([S:20]([CH2:22][CH3:23])=[O:21])[C:16]([O:24][CH3:25])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:31])([CH3:4])([CH3:3])[CH3:2].C(N1CCCCC2C(C3SC=CC=3)=C3C4C=C(N5C=C(C[C@@H](O)C[OH:59])N=N5)C(OC)=CC=4CCN3C=2C1=O)(C)(C)C.N1C=CN=C1.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.OS([O-])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O>ClCCl>[C:1]([N:5]1[CH2:30][CH2:29][CH2:28][CH2:27][C:8]2[C:9]([Br:26])=[C:10]3[C:19]4[CH:18]=[C:17]([S:20]([CH2:22][CH3:23])(=[O:59])=[O:21])[C:16]([O:24][CH3:25])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:31])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 16218505N,N,N-Tributylbutan-1-aminium hydrogen sulfate sulfate 2-sulfodioxidan-1-ide (5/1/1/2)HCID 58124920HCID 58124920, compoundHCID 58124951HCID 58124951, compound

Product 1

HCID 66919892HCID 66919892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 350 mg of 23d, and 20g of Mn(III)TPPP(OAc) and 75 mg of imidazole in 20 ml of dichloromethane were treated with tetrabutylammonium oxone, according to a described procedure; D. Mohajer et al., Tetr. Letters, 45, 3811 (2004). This provide after work-up, and chromatographic purification on silicagel (using a gradient of CH2Cl2 and ethyl acetate as eluent) 160 mg of crystalline 23e (triturated with diisopropyl ether); Mp 227° C. Rf (CH2Cl2-ethyl acetate 1/1) 0.61. LC-MS-ESI: [M+1] 522.97 and 524.99. NMR (CDCl3) δ 1.28 (t, 3, ethyl), 3.38 (q, 2, ethyl), 1.58 (s, 9, tertC4H9), 4.00 (s, 3, OCH3), 8.89 and 6.89 (2×s, 2, Ar—H), 4.50 and 3.85 (2×m, 2, CH2), 3.80 and 3.50 (2×m, 2, CH2), 3.05 (m, 2, CH2), 2.70 (m, 2, CH2) 1.90-1.65 (2×m, 4, 2×CH2).

Workup

  1. customThis provide
  2. customafter work-up, and chromatographic purification on silicagel (

Sources & evidence

ORD record
ord-ef2c96293de84430b0be27a2383873f5
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…