Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]=1[O:13][CH3:14])C=O)([CH3:4])([CH3:3])[CH3:2].[C:19]1([CH2:25][CH2:26][CH2:27][NH2:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:29]([O:31][P:32]([O-:36])[O:33][CH2:34][CH3:35])[CH3:30].[CH2:37]1COCC1>>[C:15]([C:11]1[CH:10]=[C:7]([CH:27]([NH:28][CH2:37][P:32](=[O:36])([O:33][CH2:34][CH3:35])[O:31][CH2:29][CH3:30])[CH2:26][CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[O:13][CH3:14])([CH3:16])([CH3:17])[CH3:18]Participants
Procedure
This aldehyde was reacted with 0.63 g (4.68 mmol) 3-phenylpropylamine in 25 ml THF, then 0.65 g (4.68 mmol) diethylphosphite was added and the resulting mixture heated at i10° C. for 4 h. Purification by column chromatography gave 0.9 g (37% of a yellow oil). IR (film) 3400 cm-1 (broad): NH, 1440: tert-Bu, 1220: P=O, 1020: P--O--C. NMR (CDCl3): δ=7.24 and 7.14 (2 m, 5H) phenyl H 7.26 (d, JP-H =2 Hz, 2H): aromatic H, 3,5 di-tert-butyl-4-hydroxyphenyl 4.05, 3.93 and 3.79 (3 m, 4H): P--O--CH2 --CH3 3.95 (d, JP-H =19 Hz, 1H): CH--PO3ET2 3.66 (s, 3H): Ph--O--CH3 2.66 and 2.59 (2 m, 4H): NH--CH2 --CH2 --CH2 --Ph 1.79 (m, 3H): NH and NH--CH2 --CH2 --CH2 --Ph 1.42 (s, 18H): tert-Bu 1.27 and 1.10 (2t, J=7 Hz, 6H): P--O--CH2 --CH3MS: m/e=504: M+ +366:M+ --PO3Et2
Workup
- temperaturethe resulting mixture heated at i10° C
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-b3248921defb4c6a8d30d19c0d84be8d
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05424303
Linked notes
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