Imidazole → HCID 12136312, compound

HRID 2224089Notes

Reaction equation

HRID 2224089 reaction equation
[NH2:1][C@@H:2]1[C:14]2[C:6](=[CH:7][C:8]3[O:12][CH2:11][O:10][C:9]=3[CH:13]=2)[C@@H:5]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([OH:23])=[C:17]([O:24][CH3:25])[CH:16]=2)[C@H:4]2[C:26](=[O:29])[O:27][CH2:28][C@H:3]12.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].N1C=CN=C1>CN(C)C=O>[NH2:1][C@@H:2]1[C:14]2[C:6](=[CH:7][C:8]3[O:12][CH2:11][O:10][C:9]=3[CH:13]=2)[C@@H:5]([C:15]2[CH:16]=[C:17]([O:24][CH3:25])[C:18]([O:23][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[C:19]([O:21][CH3:22])[CH:20]=2)[C@H:4]2[C:26](=[O:29])[O:27][CH2:28][C@H:3]12

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10927468(5R,5aR,8aS,9S)-9-Amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Product 1

HCID 12136312HCID 12136312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 63.4 mmol solution of (5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one, 111.8 mmol of tert-butyldimethylsilyl chloride and 510 mmol of imidazole in 1.6 l of anhydrous dimethylformamide is stirred for 20 hours at ambient temperature. The reaction mixture is then washed with 2 l of water then 1 l of ether. The ether phase is then decanted and the aqueous phase extracted with ether. The organic phases are then dried on magnesium sulfate, are filtered and concentrated under reduced pressure. The expected product is obtained by recrystallization in a benzene/heptane mixture.

Workup

  1. washThe reaction mixture is then washed with 2 l of water
  2. customThe ether phase is then decanted
  3. extractionthe aqueous phase extracted with ether
  4. customThe organic phases are then dried on magnesium sulfate
  5. filtrationare filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10a982c20bce46c08c3545242214b278
Source dataset
uspto-grants-2008_05
Patent number
US07378419B2

Reaction notes

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