Triethylsilane → 2-[cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxymethyl)cyclohexylmethoxy]-2-methylpropionic acid

HRID 854662Notes

Reaction equation

HRID 854662 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21]C(C)(C)C)=[O:20])[CH2:11]1)(C(C)(C)C)(C)C.[SiH](CC)(CC)CC.[CH3:35][C:36]1[O:40][C:39]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)=[N:38][C:37]=1[CH:48]=O>C(#N)C>[CH3:35][C:36]1[O:40][C:39]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)=[N:38][C:37]=1[CH2:48][O:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:26])([CH3:27])[C:19]([OH:21])=[O:20])[CH2:11]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 58934190HCID 58934190, compoundHCID 131726568Tert-butyl 2-[cis-3-(tert-butyldimethylsilanyloxymethyl)cyclohexylmethoxy]-2-methylpropionate

Product 1

HCID 690210082-[cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxymethyl)cyclohexylmethoxy]-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

50 mg of tert-butyl 2-[cis-3-(tert-butyldimethylsilanyloxymethyl)cyclohexyl-methoxy]-2-methylpropionate are added to a mixture of 20 mg of BiBr3 and 30 mg of HSiEt3 in 0.5 ml of acetonitrile. 38 mg of 5-methyl-2-p-tolyloxazole-4-carbaldehyde in 0.2 ml of acetonitrile are added dropwise, and the mixture is stirred at room temperature overnight. The resulting black solid is filtered and the filtrate is concentrated and taken up in 1 ml of trifluoroacetic acid. The solution is stirred at room temperature overnight. The solvent is distilled off under reduced pressure and the residue is purified by HPLC. This gives 3.4 mg of 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxymethyl)cyclohexylmethoxy]-2-methylpropionic acid as a colorless oil. C24H33NO5 (415.24); MS (ES−): 414.25 (M−H+).

Workup

  1. filtrationThe resulting black solid is filtered
  2. concentrationthe filtrate is concentrated
  3. stirringThe solution is stirred at room temperature overnight
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-d3161e9f0b47438fa74f40d00fbbcb57
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

Loading…