Ammonium Chloride → 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol

HRID 431734Notes

Reaction equation

HRID 431734 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23](O)=[O:24])=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][OH:24])=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 18761448[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acid

Product 1

HCID 187614142-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanolYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3-THF complex (1.0 M sol., 0.13 mL, 0.13 mmol) was added to a solution of [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acid (40.0 mg, 0.11 mmol) in THF (5 mL) under N2 atmosphere and stirred overnight. The reaction mixture was treated with saturated aqueous NH4Cl (1 mL) and extracted with AcOEt (20 mL), The organic layer was washed with saturated aqueous NaCl (5 mL), dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography (25% AcOEt-Petroleum ether) afforded 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol (21.2 mg, 53%) as a dark red solid. M.p. 128-130° C.; 1H NMR (CDCl3, 500 MHz) δ 8.24 (d, 9.0, 1H), 7.88 (d, 8.0, 1H), 7.66 (t, 7.5, 1H), 7.60 (t, 7.5, 1H), 7.45 (d, 7.5, 2H), 7.41 (t, 7.5, 2H), 7.35 (t, 7.5, 1H), 6.92 (s, 1H), 4.87 (brs, 1H), 4.50 (d, 5.0, 2H), 4.05 (t, 8.5, 2H), 3.40 (t, 7.0, 2H), 1.84 (brs, 1H); IR (neat) 3406, 2936, 2892, 1594, 1519, 1435, 1342, 1124, 1036, 912, 823, 752, 699 cm−1. FABMS (NBA) m/z 322 (M−CO2+), ESMS m/z 323 (M−CO2+H+), 645 ((M−CO2)×2+H+).

Workup

  1. extractionextracted with AcOEt (20 mL)
  2. washThe organic layer was washed with saturated aqueous NaCl (5 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e863e0401ec4837ad63822ae71cf84a
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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