Benzyl Alcohol → HCID 53979657, compound

HRID 989642Notes

Reaction equation

HRID 989642 reaction equation
C([C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][CH:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10](=[O:14])[N:11]([CH3:13])[CH2:12][C:6]=2[CH:5]=1)(O)=O.C([N:24]([CH2:27]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.[CH2:46]([OH:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C1(C)C=CC=CC=1>[CH2:46]([O:53][C:27]([NH:24][C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][CH:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10](=[O:14])[N:11]([CH3:13])[CH2:12][C:6]=2[CH:5]=1)=[O:36])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 53965647HCID 53965647, compound

Product 1

HCID 53979657HCID 53979657, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution stirred under argon at room temperature of methyl (±)-8-carboxy-2-methyl-3-oxo-2,3,4,5-tetrahydro-2-benzazepine-4-acetate (0.30 g, 1 mmol) and triethylamine (0.16 mL, 1.2 mmol) in toluene was added diphenylphosphorylazide (0.31 g, 1.2 mmol). The resulting mixture was heated at 80° C. for 1 h, then was allowed to cool, and benzyl alcohol (0.22 g, 2 mmol) was added. The mixture was heated at 80° C. for 4 h, then was concentrated to remove the toluene. The residue was dissolved in EtOAc, and the solution was washed sequentially with 5% aqueous NaHCO3, 1N HCl, and brine. Drying (MgSO4), concentration, and chromatography (silica gel, 1% MeOH/CH2Cl2) gave the title compound as a colorless solid (0.20 g, 47%): 1H NMR (CDCl3) δ7.40-7.30 (m, 6H), 7.06 (dd, J=8.3, 2 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H), 6.65 (br s, 1H), 5.28 (d, J=16.7 Hz, 1H), 5.20 (s, 2H), 3.80 (m, 1H), 3.79 (d, J=16.7 Hz, 1H), 3.70(s, 3H), 3.03 (s, 3H), 3.00 (m, 2H), 2.88 (m, 1H), 2.41 (dd, J=16.8, 5.3, 1H).

Workup

  1. temperatureto cool
  2. temperatureThe mixture was heated at 80° C. for 4 h
  3. concentrationwas concentrated
  4. customto remove the toluene
  5. dissolutionThe residue was dissolved in EtOAc
  6. washthe solution was washed sequentially with 5% aqueous NaHCO3, 1N HCl, and brine
  7. customDrying
  8. concentration(MgSO4), concentration, and chromatography (silica gel, 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f8541fe67d76457ab61b963dc6f0c8e1
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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