Methanol → [5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester

HRID 1955250Notes

Reaction equation

HRID 1955250 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:21]([O-:23])=[O:22])=[C:16]([CH:20]=1)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:26]([CH2:29]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.[CH3:48][OH:49]>C1C=CC=CC=1.O1CCCC1>[CH3:48][O:49][C:29](=[O:38])[NH:26][C:16]1[CH:20]=[C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:14][C:15]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 127191835-(2-Benzyloxy-ethoxy)-2-nitro-benzoic acid

Product 1

HCID 53935046[5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-benzyloxy-ethoxy)-2-nitro-benzoic acid (5.98 g, 18.85 mmol) in benzene (100 ml) and anhydrous tetrahydofuran (25 ml) was added triethyl amine (3.07 ml, 22 mmol) followed by diphenylphosphoryl azide (4.74 ml, 22 mmol). The reaction was stirred at room temp for 15 min, and then refluxed under nitrogen for 4 h. methanol (3 ml, 74.06 mmol) was added, and the reaction was refluxed for 18 h. The solvent was evaporated, and the oil chromatographed on silica gel eluting with 25% ethyl acetate/hexanes to give [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester (6.12 g, 94%) as an oil. Analysis calculated for C17H18N2O6 : C, 58.96; H, 5.24; N, 8.09. Found: C, 58.94; H, 5.11; N, 7.87

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed for 18 h
  3. customThe solvent was evaporated
  4. customthe oil chromatographed on silica gel eluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-969811f1b9d04f52b8d184c6f420f71f
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…