Triphenylphosphine → HCID 59946060, compound

HRID 1490252Notes

Reaction equation

O[CH:2]([CH3:17])[C:3]#[C:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:37]([C:44]([NH:46][O:47][C:48]([O:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:49])=[O:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>[O:50]([C:48]([O:47][N:46]([CH:2]([CH3:17])[C:3]#[C:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:6]1)[C:44]([O:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:45])=[O:49])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

Conditions

Temperature: 0 °C

Procedure

trans-2-(3-Hydroxy-but-1-ynyl)-5-(4-fluorophenyl) tetrahydrofuran (205, 210 mg, 0.89 mmol), triphenylphosphine (288 mg, 1.1 mmol) and N,O-bis(phenoxycarbonyl)hydroxylamine (283 mg, 1.1 mmol) were dissolved in dry THF (5 mL). The solution was cooled to 0° C. under dry argon, and diisopropylazodicarboxylate (216 mL, 1.1 μmol) was added dropwise. Stirring was continued for 1 hour at the same temperature. The solvent was evaporated and the residue was purified via flash column chromatography (eluent, 30% ethyl acetate in hexane) to yield 250 mg (57%) of trans-2-{3-(N-phenoxycabonyloxy-N-phenoxycarbonyl-amino)-but-1-ynyl}-5-(4-fluorophenyl) tetrahydrofuran (206). 1H-NMR (CDCl3) δ 7.15-7.45 (12H, m), 7.02 (2H, t, J=8.6 Hz), 5.32 (1H, q J=7.0 Hz), 5.07 (1H, t, J=6.8 Hz), 4.96 (1H, t, J=5.7 Hz), 2.25-2.50 (2H, m), 2.05-2.20 (1H, m), 1.70-1.85 (1H, m), 1.66 (3H, d, J=7.0 Hz).

Workup

customThe solvent was evaporated
customthe residue was purified via flash column chromatography (eluent, 30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-907c0e7ebd6e4194b76434bd159ea3d7
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681966

Reaction notes

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