Triphenylphosphine → HCID 15946645, compound
Reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:34]([O:41][C@H:42]1[C@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([CH2:56][O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:45][C@H:44]([CH2:65][P:66]([O:71][CH2:72][CH3:73])(=[O:70])[O:67][CH2:68][CH3:69])[C@@H:43]1O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.P([N:91]=[N+:92]=[N-:93])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1>C1COCC1>[N:91]([C@H:43]1[C@@H:42]([O:41][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([CH2:56][O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:45][C@@H:44]1[CH2:65][P:66]([O:71][CH2:72][CH3:73])(=[O:70])[O:67][CH2:68][CH3:69])=[N+:92]=[N-:93]Participants
6
Procedure
DIAD (2.4 mL, 12.4 mmol) was added dropwise to a cooled (−5° C.) solution of Ph3P (3.1 g, 11.7 mmol) in THF (50 mL). After 30 min, a solution of 2 (5.57 g, 9.5 mmol) in THF (20 mL) was added. After an additional 10 min, diphenyl phosphorazidate (DPPA; 2.4 mL, 11.31 mmol) was added and the reaction mixture was allowed to attain rt. After stirring overnight, the solvent was evaporated and the residue was purified by silica gel chromatography to give 3 (5.0 g, 8.2 mmol, 86%) as a colorless oil. 13C-NMR (CDCl3) 138.17, 137.92, 137.38, 128.6-127.7, 78.2, 74.3, 73.9, 73.7, 73.5, 72.4, 69.5, 68.8, 62.2, 62.1, 62.0, 61.9, 61.0, 60.9, 27.9 (d, J=141 Hz), 16.5, 16.4; 31P-NMR (CDCl3) 27.9.
Workup
- waitAfter an additional 10 min
- customto attain rt
- customthe solvent was evaporated
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-1614b4e9a8454057bc6fc749c07f89ea
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08062641B2
Reaction notes
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