Imidazole → HCID 66701965, compound

HRID 424653Notes

Reaction equation

HRID 424653 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[NH2:14][C:15]1[N:20]=[C:19]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=[C:17]([NH:29][C@H:30]([CH3:33])[CH2:31][OH:32])[CH:16]=1>CN(C=O)C>[CH2:22]([S:21][C:19]1[N:18]=[C:17]([NH:29][C@H:30]([CH3:33])[CH2:31][O:32][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH:16]=[C:15]([NH2:14])[N:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 66702018HCID 66702018, compound

Product 1

HCID 66701965HCID 66701965, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.29 g) was added to a solution of tert-butyldimethylsilyl chloride (0.34 g) and the subtitle product of step i) (0.6 g) in DMF (10 ml). The reaction was stirred for 24 h before addition of a further equivalent of tert-butyldimethylsilyl chloride and imidazole. After stirring for an additional 24 h the reaction mixture was partitioned between EtOAc (100 ml) and H2O (200 ml). The aqueous was extracted further with EtOAc (3×100 ml), the organics combined, washed with H2O (100 ml), brine (100 ml), dried (MgSO4) and concentrated to a crude solid. This material was purified by column chromatography (1:1 Et2O/iso-hexane) to afford the subtitle compound as a yellow oil. Yield: 0.50 g.

Workup

  1. customwas partitioned between EtOAc (100 ml) and H2O (200 ml)
  2. extractionThe aqueous was extracted further with EtOAc (3×100 ml)
  3. washwashed with H2O (100 ml), brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a crude solid
  6. customThis material was purified by column chromatography (1:1 Et2O/iso-hexane)

Sources & evidence

ORD record
ord-1d7811ba988e4c248b53375dbb9dc11a
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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