Triphenylphosphine → HCID 11731204, compound

HRID 747766Notes

Reaction equation

HRID 747766 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[I:32])[C:27]#[N:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:24]1[CH:25]=[C:26]([C:27]#[N:28])[CH:29]=[CH:30][C:31]=1[I:32])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 109446813-Hydroxy-4-iodobenzonitrileHCID 11045079HCID 11045079, compound

Product 1

HCID 11731204HCID 11731204, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.16 g (32.8 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-hydroxybutanoate was dissolved in 100 ml of toluene. 10.5 g (42.7 mmol) of 3-hydroxy-4-iodobenzonitrile, 11.2 g (42.7 mmol) of triphenylphosphine and 7.4 g (42.7 mmol) of N,N,N′,N′-tetramethylazodicarboxyamide were added to the solution under cooling with ice, and they were stirred at room temperature overnight. The solvent was distilled off, and the residue was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=2:1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c96a0ee7ceb94609808e70aa637b32a8
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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