Imidazole → HCID 54547927, compound

HRID 1755824Notes

Reaction equation

HRID 1755824 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([N:16]1[CH2:22][CH2:21][CH:20]([C@H:23]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:24])[CH:19]([OH:34])[CH:18]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:17]1=[O:42])[CH3:15])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:48](Cl)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49].O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([N:16]1[CH2:22][CH2:21][CH:20]([C@H:23]([CH2:25][O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:24])[CH:19]([O:34][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH:18]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:17]1=[O:42])[CH3:15])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 54358663HCID 54358663, compound

Product 1

HCID 54547927HCID 54547927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A single isomer of the alcohol (62) is dissolved in DMF and treated with imidazole (2 equivalents) and t-butyldimethylsilyl chloride (1.05 equivalents) at room temperature overnight. The reaction mixture is poured into water and extracted with ethyl acetate. The combined organic extracts are dried over MgSO4 and evaporated at reduced pressure. The residue is purified by flash chromatography to give (63).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. customevaporated at reduced pressure
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-8cf4fb6b63464f29ac43697d4dd45e4b
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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