Triacetoxyperiodinane → HCID 18962496, compound

HRID 1707765Notes

Reaction equation

HRID 1707765 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:45][CH2:46][CH3:47])=[N:5][C:4]=1[CH:48]=[CH2:49].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:45]([C:6]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:24]=[N:23][N:22]=3)=[CH:13][CH:14]=2)[C:3]([CH:2]=[O:1])=[C:4]([CH:48]=[CH2:49])[N:5]=1)[CH2:46][CH3:47]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 18962493HCID 18962493, compound

Product 1

HCID 18962496HCID 18962496, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-hydroxymethyl-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-4-vinylimidazole (470 mg, 0.73 mmol, 1 eq), Dess-Martin periodinane (J. Org. Chem. (1983) 48, 4155) (341 mg, 0.80 mmol, 1.1 eq) and methylene chloride (10mL) were mixed and stirred under nitrogen overnight. The solvent was removed in vacuo and the residue flash chromatographed in 3:2 hexane ethyl acetate over silica gel to yield 310 mg (66%) of a white glass. NMR (DMSO-d6) δ 9.91 (s,1H); 7.80 (d,1H,J=7Hz); 7.61 (t,1H, J=7Hz); 7.54 (t,1H,J=7Hz); 7.48-7.22(m,10H); 7.20 (d,1H,J=9Hz); 7.06 (d,2H,J=9Hz); 7.00-6.75 (m,8H); 6.15 (d of d,1H,J=17,3 Hz); 5.52 (s,2H); 5.47 (d of d,1H,J=12,3 Hz); 2.49 (t,2H,J=7Hz); 1.57 (t of q,2H,J=7,7Hz); 0.79 (t,3H,J=7Hz). IR (neat) 1658 cm-1. Anal. calcd. for C42H36N6O.(H2O)0.5 : C, 77.63; H, 5.74; N, 12.93. Found: C, 77.53; H, 5.73; N, 12.64. ##STR81##

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue flash chromatographed in 3:2 hexane ethyl acetate over silica gel

Sources & evidence

ORD record
ord-359b51bb62514dffa5a0d0ad3ed8ef5b
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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