Triphenylphosphine → HCID 54510683, compound

HRID 747778Notes

Reaction equation

HRID 747778 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:20][CH2:21][CH2:22][OH:23])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([C:26]1[CH:27]=[C:28](O)[CH:29]=[CH:30][CH:31]=1)#[N:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:20][CH2:21][CH2:22][O:23][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([C:24]#[N:25])[CH:31]=1)[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53858440N-[(1,1-Dimethylethoxy)carbonyl]-5-hydroxy-D-norvaline phenylmethyl ester

Product 1

HCID 54510683HCID 54510683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.77 g (21 mmol) of benzyl 2-(2R)-t-butoxycarbonylamino-5-hydroxypentanoate was dissolved in 105 ml of tetrahydrofuran. 2.74 g (23 mmol) of 3-cyanophenol, 6.6 g (25 mmol) of triphenylphosphine and 10 g (23 mmol) of diethyl azodicarboxylate (40% solution in toluene) were added to the solution, and they were stirred at room temperature for one hour. The solvent was distilled off, and the residue was treated with ethyl acetate as the extractant in an ordinary manner. The solvent was distilled off, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was treated with ethyl acetate as the extractant in an ordinary manner
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-6917299838a641ee901d8d37343aaa7d
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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