Imidazole → HCID 11121845, compound

HRID 1243193Notes

Reaction equation

HRID 1243193 reaction equation
[OH:1][CH2:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:14](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[C:27]([Si:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:1][CH2:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 5324733Roche ester (R)

Product 1

HCID 11121845HCID 11121845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (R)-(−)-3-hydroxy-2-methylpropionate (0.82 g, 6.92 mmol) (Aldrich) was dissolved in dichloromethane (8 mL, dried over molecular sieves). Imidazole (0.67 g, 9.68 mmol) (Aldrich) was added. When all had dissolved, tert-butyldiphenysilyl chloride (1.80 mL, 6.92 mmol) (Aldrich) was added and the mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with additional dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give methyl (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionate as an oil. (Yield 2.42 g, 98%).

Workup

  1. dissolutionWhen all had dissolved
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d011d5bfef5c43a4834cdec09d36dbb7
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

Loading…