Triethylamine → ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate

HRID 431732Notes

Reaction equation

HRID 431732 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:15]([N+:29]([O-:31])=[O:30])[CH:14]=1.CCN(CC)CC>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:15]([N+:29]([O-:31])=[O:30])[CH:14]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11460008Ethyl (4-amino-2-nitronaphthalen-1-yl)acetate

Product 1

HCID 59060232ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetateYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (1.56 mL, 10.94 mmol) was added to a solution of ethyl (4-amino-2-nitronaphthalen-1-yl)acetate (1.0 g, 3.65 mmoml) and Et3N (0.56 mL, 4.01 mmol) in dry CH2Cl2 (20 mL) slowly that was at 0° C. under N2 atmosphere. The mixture was heated to reflux for 3 days and concentrated. The residue was dissolved in AcOEt (50 mL), and washed with H2O (10 mL) and saturated aqueous NaCl (25 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography (20% AcOEt-Petroleum ether to CHCl3) afforded ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate (0.39 g, 26%) as an orange solid. M.p. 160-164° C.; 1H NMR (CDCl3, 500 MHz) δ 8.09 (d, 8.5, 1H), 7.88 (d, 8.0, 1H), 7.66 (t, 8.0, 1H), 7.60 (t, 7.0, 1H), 7.46 (d, 7.5, 2H), 7.41 (t, 7.5, 2H), 7.35 (t, 7.5, 1H), 7.07 (s, 1H), 4.92 (brs, 1H), 4.52 (d, 4.0, 2H), 4.24 (s, 2H), 4.19 (q, 7.0, 2H), 1.26 (t, 7.5, 3H); IR (neat) 3397, 2927, 1723, 1594, 1537, 1515, 1439, 1333, 1200, 1124, 1027, 823, 752, 703 cm−1.

Workup

  1. customthat was at 0° C. under N2 atmosphere
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 days
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in AcOEt (50 mL)
  6. washwashed with H2O (10 mL) and saturated aqueous NaCl (25 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d0a191d33b746739998772415565e74
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

Loading…