1,4-Dimethoxynaphthalene → HCID 86760125, compound

HRID 1790292Notes

Reaction equation

HRID 1790292 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH3:18])=[CH:9][CH:8]=1.[F:19][C:20]([F:30])([F:29])[C:21]([NH:23][C@@H:24]([C:26](O)=[O:27])[CH3:25])=[O:22]>ClCCl>[CH3:18][O:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([O:6][CH3:5])=[CH:8][C:9]=1[C:26](=[O:27])[C@H:24]([NH:23][C:21](=[O:22])[C:20]([F:19])([F:29])[F:30])[CH3:25]

Participants

5

Reactant 3

HCID 823371,4-DimethoxynaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 13774519HCID 13774519, compound

Product 1

HCID 86760125HCID 86760125, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of AlCl3 (3.8 g, 28.6 mmol) in dichloromethane (100 mL) was added a solution of 1,4-dimethoxynaphthalene (4.88 g, 25.9 mmol) in dichloromethane (50 mL). To this mixture was added a solution of (R)-N-trifluoroacetylalanine (16 g, 86.5 mmol) in CH2Cl2 (50 mL); this mixture was stirred at room temperature for 3 h. The reaction mixture was poured slowly into ice (200 g) to quench the reaction and the organic layer was separated and dried (MgSO4). The solvent was evaporated and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9) to give a yellow oil (3 g): 1H NMR (DMSO-d6) δ 1.24 (d, 3H, CH3), 3.93 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 5.51 (m, 1H), 6.99 (s, 1H, Ar—H), 7.96 (m, 2H, Ar—H), 8.17 (m, 2H, Ar—H), 9.83 (d, NH); MS 356 (M+1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9)

Sources & evidence

ORD record
ord-0893e4388b4946148f4fb6c36f0aa994
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

Loading…