P,P-Diphenylphosphinic azide → HCID 178450065, compound

HRID 480491Notes

Reaction equation

HRID 480491 reaction equation
[OH:1][C:2](C1C=C2C(=CC=1)C=C(C(OC)=O)C=C2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].[OH:44][C:45]([C:73]1[CH:74]=[C:75]2[C:80](=[CH:81][CH:82]=1)[CH:79]=[C:78](C(O)=O)[CH:77]=[CH:76]2)(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)C(C)C.C(=O)([O-])[O-].[NH4+].[NH4+].C1(P([N:106]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C.O.C(N(CC)CC)C>[OH:1][C:2]([C:78]1[CH:79]=[C:80]2[C:75](=[CH:76][CH:77]=1)[CH:74]=[C:73]([C:45]([NH2:106])=[O:44])[CH:82]=[CH:81]2)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 199401P,P-Diphenylphosphinic azideHCID 517111Ammonium CarbonateHCID 187691016-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acidHCID 22285069methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate

Product 1

HCID 178450065HCID 178450065, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In a manner to that described in Example 9-(i), methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (2.0 g) was converted to 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid and this compound was dissolved in DMF (10 mL). Ammonium carbonate (558 mg), diphenylphosphorylazide (0.91 mL) and triethylamine (0.98 mL) were added and the resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluent; hexane:THF=1:2) to give the titled compound (1.96 g) as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluent; hexane:THF=1:2)

Sources & evidence

ORD record
ord-3f62ff07be0b4a80b530385aa69aaaff
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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