Imidazole → Acetate hexane

HRID 975270Notes

Reaction equation

HRID 975270 reaction equation
N1C=CN=C1.C[C@H]1[C@H](O)C(=O)OC[C@]23[C@H](O[C@H]4[C@]5(OC5)[C@]2(C)[C@@H](C4)[O:18][C:16](=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][C@H:11]([C@H:41](O)[CH3:42])OCC1)C=C(C)CC3.[Si](Cl)(C(C)(C)C)(C)C>CN(C)C=O>[C:16]([O-:18])(=[O:17])[CH3:15].[CH3:42][CH2:41][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9915017Roridin A

Product 1

HCID 22139250Acetate hexane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

Preparation of 13'-O-tert-butyldimethylsilyl-Roridin A. 100 mg (1.47 mmol) of imidazole was added to a solution of 232 mg (0.436 mmol) of Roridin A in 3 ml of dry dimethylformamide. The mixture was cooled to -5° C. and then 72 mg (0.478 mmol) of tert-butyldimethylsilyl chloride (Aldrich Chemical Co.) was added. The resultant mixture was stirred at -5° C. to 5° C. for 4 hours and then concentrated. The residue was chromatographed on silica gel, eluting first with 30% ethyl acetate/hexane, next with 50% ethyl acetate/hexane and finally with 70% ethyl. acetate/hexane, to afford 137 mg of the product as a foamy white solid (49%): TLC-Rf 0.32 (30% ethyl acetate/hexane).

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed on silica gel
  3. washeluting first with 30% ethyl acetate/hexane, next with 50% ethyl acetate/hexane and finally with 70% ethyl

Sources & evidence

ORD record
ord-7d21b25d193940dfa66b28111f08dbf8
Source dataset
uspto-grants-1997_03
Patent number
US05608060

Reaction notes

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