Triphenylphosphine → HCID 131733851, compound

HRID 708539Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22][N:23]1[N:27]=[C:26]([CH2:28]O)[C:25]([CH2:30][NH:31][S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])=[N:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22][N:23]1[N:27]=[C:26]2[CH2:28][N:31]([S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[CH2:30][C:25]2=[N:24]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a soln of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((4-(hydroxymethyl)-5-((2-nitrophenylsulfonamido)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (165 mg, 0.237 mmol), and triphenylphosphine (91.6 mg, 0.349 mmol) in THF (11.9 mL) at 0° C. was added DIAD (72 μL, 0.35 mmol), drop-wise. After 3 h, more triphenylphosphine (46.4 mg, 0.177 mmol) was added, whereupon it was cooled to 0° C. followed by addition of DIAD (37 μL, 0.18 mmol). After stirring at rt for 2.5 h it was concentrated in vacuo and purified via silica gel chromatography (EtOAc-Heptane, 0-100%) to afford the title compound (318 mg), which was contaminated with triphenylphosphine oxide. Rt=0.93 min, m/z=678.3 (M+1) Method 2m_acidic.

Workup

concentrationwas concentrated in vacuo
custompurified via silica gel chromatography (EtOAc-Heptane, 0-100%)

Sources & evidence

ORD record: ord-cf4697cbbfb24ce69737eb1c756ebeda
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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