1-Methylimidazole → HCID 70078934, compound

HRID 743999Notes

Reaction equation

HRID 743999 reaction equation
[CH2:1]([C:5]1[N:6]([O:42][CH2:43][O:44][CH:45]([Si:47]([CH3:50])([CH3:49])[CH3:48])[CH3:46])[C:7]([C:10]2([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH2:36][C:37]([O:39]CC)=[O:38])S[C:11]2([CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]([O:15]C)=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].P(OC)(OC)OC.CN1C=CN=C1>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[N:6]([O:42][CH2:43][O:44][CH:45]([Si:47]([CH3:48])([CH3:49])[CH3:50])[CH3:46])[C:7](/[C:10](/[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH2:36][C:37]([OH:39])=[O:38])=[C:11](\[CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)/[C:13]([OH:15])=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 8472Trimethyl phosphiteHCID 86749848HCID 86749848, compound

Product 1

HCID 70078934HCID 70078934, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl (2RS,3RS)-3-(2-n-Butyl-1-trimethylsilylethyloxymethoxy-1H-imidazol-5-yl)-3-(2-ethoxycarbonylmethoxy-4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)thiirane-2-carboxylate (411 mg, 0.58 mmol) and trimethyl phosphite, freshly distilled from Na (2 ml, 6 mmol) with 1-methylimidazole (100 μl) in CHCl3 (4 ml) were kept at reflux temperature for 48 h under argon. The solvent and excess trimethyl phosphite were removed under reduced pressure (high vacuum) and the residue chromatographed on silica gel (80% EtOAc/hexanes) to give the title compound. (256 mg, 65%)

Workup

  1. temperatureat reflux temperature for 48 h under argon
  2. customThe solvent and excess trimethyl phosphite were removed under reduced pressure (high vacuum)
  3. customthe residue chromatographed on silica gel (80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4c35e69ea0bd41bbbf3c1855f2fb970c
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

Loading…