Imidazole → HCID 18433594, compound

HRID 2306200Notes

Reaction equation

HRID 2306200 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1>>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18433594HCID 18433594, compound

Procedure

A mixture of 8-(tert-butoxycarbonylamino)-2-naphthol, as described above in Step A, (43.2 g, 0.167 mol), tert-butyldimethylsilyl chloride (32.7 g, 0.217 mol), and imidazole (25.0 g, 0.367 mol) in dry, degassed DMF (400 mL) was stirred, under argon, at ambient temperature for 30 min. The solvent was removed under reduced pressure and the residue was partitioned between H2O (1 L) and Et2O (2 L). The aqueous layer was extracted further with Et2O (1 L) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—50% CH2Cl2 to yield the desired product as a pale solid.

Workup

  1. customin dry
  2. customdegassed DMF (400 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between H2O (1 L) and Et2O (2 L)
  5. extractionThe aqueous layer was extracted further with Et2O (1 L)
  6. dry with materialthe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography on silica
  10. washeluting with hexane—50% CH2Cl2

Sources & evidence

ORD record
ord-05bb82fd0e4c41ce86df3608692f2e16
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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