Imidazole → HCID 69507500, compound

HRID 1357416Notes

Reaction equation

HRID 1357416 reaction equation
[O:1]=[C:2]([C@H:25]([CH3:41])[C@@H:26]([O:32][C:33]([O:35][CH2:36][C:37]([Cl:40])([Cl:39])[Cl:38])=[O:34])[C@@H:27]([CH3:31])[CH2:28][CH:29]=[CH2:30])[C:3]([CH3:24])([CH3:23])[C@@H:4]([OH:22])[C@H:5]([CH3:21])[C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])=[O:7].N1C=CN=C1.[CH2:47]([Si:49](Cl)([CH2:52][CH3:53])[CH2:50][CH3:51])[CH3:48].O>CN(C)C=O>[O:1]=[C:2]([C@H:25]([CH3:41])[C@@H:26]([O:32][C:33]([O:35][CH2:36][C:37]([Cl:39])([Cl:40])[Cl:38])=[O:34])[C@@H:27]([CH3:31])[CH2:28][CH:29]=[CH2:30])[C:3]([CH3:23])([CH3:24])[C@@H:4]([O:22][Si:49]([CH2:52][CH3:53])([CH2:50][CH3:51])[CH2:47][CH3:48])[C@H:5]([CH3:21])[C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])=[O:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 13819ChlorotriethylsilaneHCID 59922965(4S)-3-[(2S,3S,6R,7S,8S)-5-oxo-3-hydroxy-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoyl]-4-benzyloxazolidinone

Product 1

HCID 69507500HCID 69507500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4S)-3-[(2S,3S,6R,7S,8S)-5-oxo-3-hydroxy-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoyl]-4-benzyloxazolidinone (2.6 g), imidazole (0.48 g), and triethylsilyl chloride (0.68 g) in 5 mL of dimethylformamide is stirred for 2 hours at ambient temperature, then poured into water and extracted with ether. The extract is washed with sat. aq. NaCl, dried over MgSO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with sat. aq. NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product is purified by chromatography on SiO2

Sources & evidence

ORD record
ord-0c895976b0ea4c5ca0afb0c17c2e1eaf
Source dataset
uspto-grants-2003_07
Patent number
US06589968B2

Reaction notes

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