Triphenylphosphine → HCID 90800986, compound

HRID 2307831Notes

Reaction equation

[N:1]1([CH2:10][C@@H:11](O)[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:55]=[N+:56]=[N-:57])(C2C=CC=CC=2)=O)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:55]([C@H:11]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)=[N+:56]=[N-:57]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of Example 441A (1.0 g, 3.54 mmol) and triphenylphosphine (1.39 g, 5.31 mmol) in anhydrous THF (30 mL) was added diphenylphosphoryl azide (1.14 mL, 5,31 mmol) at 0° C. followed by the addition of DEAD (836 μL). The reaction mixture was stirred at 0° C. for 30 mins and at room temperature for 15 hrs. The concentrated residue was then purified by flash column chromatography on silica gel eluting with 60%-80% ethyl acetate/hexanes to provide the desired product.

Workup

customThe concentrated residue was then purified by flash column chromatography on silica gel eluting with 60%-80% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-383fc9eb5e0246528345c798aa08ccd7
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831175B2

Reaction notes

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