Imidazole → HCID 69214867, compound

HRID 131562Notes

Reaction equation

HRID 131562 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]=3[S:11][C:10]=2[CH3:25])=[O:8])[CH2:3]1.N1C=CN=C1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>ClCCl>[CH3:35][C:34]([Si:31]([CH3:33])([CH3:32])[O:1][CH:2]1[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:12]=3[S:11][C:10]=2[CH3:25])=[O:8])[CH2:3]1)([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68804449HCID 68804449, compound

Product 1

HCID 69214867HCID 69214867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step b) (1.2 g) and imidazole (0.24 g) in dichloromethane (20 ml) was added tert-butyldimethylsilyl chloride (0.54 g). After stirring at ambient temperature for 16 h the mixture was washed with water and the organics poured onto a biotage column. Gradient elution with 0 to 5% methanol in dichloromethane gave the sub-title compound as a colourless solid (1.55 g). δ 1HCDCl3 0.09 (3H,s), 0.11 (3H,s), 0.90 (9H,s), 0.99 (6H,d), 2.30 (1H,non), 2.44 (3H,s), 3.36 (3H,s), 3.54 (1H,dd), 3.64 (1H,dd), 3.75 (1H,d), 3.84 (1H,dd), 3.98 (1H,dd), 4.47 (1H,dd), 4.89 (1H,dd).

Workup

  1. washwas washed with water
  2. additionthe organics poured onto a biotage column
  3. washGradient elution with 0 to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-6e3bfa38418d478c848b4a02bdeeed3a
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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