Sodium hydride → HCID 18475834, compound

HRID 2187886Notes

Reaction equation

HRID 2187886 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].[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27]Cl.[NH4+].[Cl-]>C1COCC1.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18475834HCID 18475834, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(tert-butoxycarbonylamino)-2-naphthol, as described in Example 6, Step A, (1.80 g, 6.94 mmol) in dry THF (50 mL), at 0° C., under argon, was added NaH (305 mg of a 60% oil dispersion, 7.64 mmol). The resulting mixture was stirred for 30 min, then 2-methoxyethoxymethyl chloride (0.95 mL, 8.33 mmol) was added. The mixture was allowed to warm slowly and then stirred at ambient temperature for 18 hrs. The reaction mixture was poured into saturated aqueous NH4Cl (100 mL) and CH2Cl2 (250 mL). The organic layer was 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 −20% to 50% EtOAc to yield the desired product as a colorless oil.

Workup

  1. temperatureto warm slowly
  2. stirringstirred at ambient temperature for 18 hrs
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica
  7. washeluting with a gradient of hexane −20% to 50% EtOAc

Sources & evidence

ORD record
ord-86685d04995a45dfb298e72506236b06
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

Loading…