Triphenylphosphine → HCID 136005795, compound

HRID 915930Notes

Reaction equation

HRID 915930 reaction equation
[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=4[O:24][CH3:25])=[N:11][C:10]=3[N:9]([CH3:26])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@@H:47]1[CH2:51][CH2:50][O:49][CH2:48]1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C.O1CCCC1>[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C@H:47]5[CH2:51][CH2:50][O:49][CH2:48]5)=[CH:19][C:18]=4[O:24][CH3:25])=[N:11][C:10]=3[N:9]([CH3:26])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 641512(-)-3-Hydroxytetrahydrofuran2×HCID 136005835HCID 136005835, compound

Product 1

HCID 136005795HCID 136005795, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 10 ml tetrahydrofuran suspension of 150 ml (0.423 mmol) of the compound obtained in Example 36, 133 mg (0.508 mmol) of triphenylphosphine, 51 μl (0.635 mmol) of (R)-(−)-3-hydroxytetrahydrofuran, and 80 μl (0.508 mmol) of diethyl azodicarboxylate were slowly added at room temperature, and the mixture was stirred at room temperature for 1 hour. Further, 44 mg (0.169 mmol) of triphenylphosphine, 17 μl (0.212 mmol) of (R)-(−)-3-hydroxytetrahydrofuran, and 27 μl (0.169 mmol) of diethyl azodicarboxylate were added, and the mixture was stirred at room temperature for 1.5 hours. Then, the reaction mixture was diluted with ethyl acetate, and the dilution was washed with water and a saturated aqueous solution of sodium chloride in this order. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1˜1/2) to obtain 124 mg (69%) of the captioned compound.

Workup

  1. additionwere slowly added at room temperature
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. washthe dilution was washed with water
  4. dry with materialThe washed system was dried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1˜1/2)

Sources & evidence

ORD record
ord-03c51da25054464691384dc111c2d3f6
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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