Imidazole → HCID 18475884, compound

HRID 2187881Notes

Reaction equation

HRID 2187881 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:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.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:33]([CH3:36])([CH3:35])[CH3:34])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18475884HCID 18475884, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 8-(tert-butoxycarbonylamino)-2-naphthol, as described above in Step A, (35 g, 0.135 mol), tert-butyldiphenylsilyl chloride (40.9 g, 0.149 mmol), and imidazole (18.4 g, 0.270 mmol) in dry, degassed DMF (300 mL) was stirred, under argon, at 50° C. for 18 hrs. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (500 mL) and EtOAc (1 L). The aqueous layer was extracted further with EtOAc (300 mL) 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 a gradient of hexane −25% to 45% CH2Cl2 to yield the desired product as a pale solid.

Workup

  1. customin dry
  2. customdegassed DMF (300 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between saturated aqueous NaHCO3 (500 mL) and EtOAc (1 L)
  5. extractionThe aqueous layer was extracted further with EtOAc (300 mL)
  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 a gradient of hexane −25% to 45% CH2Cl2

Sources & evidence

ORD record
ord-5a2bec65bc8646d497e6344c14c2d6ec
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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