Nitrogen → HCID 23374569, compound

HRID 865659Notes

Reaction equation

HRID 865659 reaction equation
N#N.[C:3]1([C:9]2[CH2:10][CH2:11][CH:12](C(O)=O)[CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1>C1(C)C=CC=CC=1>[C:3]1([C:9]2[CH2:10][CH2:11][CH:12]([N:19]=[C:22]=[O:31])[CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23374552HCID 23374552, compound

Product 1

HCID 23374569HCID 23374569, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a N2 covered solution of 2.0 g (10.6 mmol) of the product from Step 2 in 40 ml of toluene was added 2.2 ml (15.9 mmol) of triethylamine followed by 3.4 ml (15.9 mmol) of diphenylphosphorylazide. After heating in an oil bath at 90° C. for 55 minutes. The reaction was allowed to cool and concentrated in vacuo. The residue was partitioned between 150 ml of 1:1 Et2O: hexane and 20 ml of pH 7 phosphate buffer. The aqueous layer was separated and washed once with 1:1 Et2O: hexane. The combined organic fractions were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed over 50 ml of silica gel (1% EtOAc: hexane) to yield 1.46 g (74.3%) of the titled product.

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 150 ml of 1:1 Et2O
  4. customThe aqueous layer was separated
  5. washwashed once with 1:1 Et2O
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed over 50 ml of silica gel (1% EtOAc: hexane)

Sources & evidence

ORD record
ord-5fd99b644ec6479cac8ea7e6dad6259a
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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