Imidazole → HCID 11121845, compound

HRID 2216990Notes

Reaction equation

HRID 2216990 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 (30.81 g; 260.8 mmol) (Aldrich) was dissolved in dichloromethane (300 mL, dried over molecular sieves). Imidazole (25.11 g; 365.1 mmol) (Aldrich) and tert-butyl-diphenylsilyl chloride (68.00 mL; 261.5 mmol) (Aldrich) were added and the mixture was stirred at room temperature for 6 hours. The reaction was diluted with additional dichloromethane (300 mL), washed with water (2×150 mL) and brine (1×150 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to yield methyl (R)-(−)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionate as an oil. (Yield 94.3 g).

Workup

  1. washwashed with water (2×150 mL) and brine (1×150 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbfec379810c4ed3b61d600fe00347e4
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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