Imidazole → HCID 69507500, compound

HRID 348255Notes

Reaction equation

HRID 348255 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-09e45b330de949739f43570a5fbac094
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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