Benzyl Alcohol → HCID 11626340, compound

HRID 1643883Notes

Reaction equation

HRID 1643883 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[CH2:11][CH:10](C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[CH2:49]([OH:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O1CCOCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:19])([F:20])[F:21])=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:44][C:47](=[O:32])[O:56][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59778157HCID 59778157, compound

Product 1

HCID 11626340HCID 11626340, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 149D (345 mg, 1.029 mmol) in dioxane (3.5 mL) was added diphenylphosphoryl azide (244 μL, 1.133 mmol) and triethylamine (170 μL, 1.236 mmol). The reaction mixture was stirred at RT for 20 min, then benzylalcohol (130 μL, 1.236 mmol) was added. The reaction was heated at 100° C. for 7 h. After cooling to RT, the reaction mixture was concentrated in vacuo, and the residue partitioned between EtOAc and water. The separated organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed (silica gel) eluting with EtOAc/hexane 0-40% to afford 149E as a clear oil (390 mg, 86%).

Workup

  1. temperatureThe reaction was heated at 100° C. for 7 h
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed (silica gel)
  9. washeluting with EtOAc/hexane 0-40%

Sources & evidence

ORD record
ord-6f99d023f4844ed3ad98d932c491806f
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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