Imidazole → HCID 131733874, compound

HRID 708899Notes

Reaction equation

HRID 708899 reaction equation
[F:1][C:2]1[C:3]([O:24][C@H:25]2[C@@H:29]([OH:30])[CH2:28][O:27][CH2:26]2)=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].N1C=CN=C1>CN(C=O)C>[Si:31]([O:30][C@H:29]1[CH2:28][O:27][CH2:26][C@H:25]1[O:24][C:3]1[C:2]([F:1])=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:4]=1[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 118092993HCID 118092993, compound

Product 1

HCID 131733874HCID 131733874, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 27E (171 mg, 0.407 mmol) in DMF (3 mL) was added TBS-Cl (307 mg, 2.034 mmol) and imidazole (138 mg, 2.034 mmol). The reaction was stirred at rt for 16 h, then quenched with H2O and extracted with EtOAc (2×). The solvent was removed and the residue was purified by flash column chromatography (0-60% EtOAc/hexanes) to give 27F (215 mg, 0.402 mmol, 99% yield). MS (ESI) m/z: 535.4 (M+H)+.

Workup

  1. customquenched with H2O
  2. extractionextracted with EtOAc (2×)
  3. customThe solvent was removed
  4. customthe residue was purified by flash column chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-33b5116c1695450a87a2daf1b99a2f55
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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