CID 406 → tert-Butyl[2,2-Dimethyl-5-(4-octanoylstyryl)-1,3-dioxan-5-yl]carbamate

HRID 1028883Notes

Reaction equation

P(=O)([O-])[O-].[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=O)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].[C:23]([O-:26])([O-])=O.[K+].[K+].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>CN(C=O)C>[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=[CH:31][C:30]2[CH:7]=[CH:5][C:6]([C:23](=[O:26])[CH2:33][CH2:29][CH2:30][CH2:31][CH2:13][CH2:12][CH3:17])=[CH:33][CH:29]=2)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 72.5 °C

Procedure

A mixture of the Wittig reagent (23, X═O) or the phosphonate (0.3 mmol), aldehyde (24) (0.33 mmol), and K2CO3 (0.9 mmol) in a mixture of THF (3 ml) and DMF (1 ml) was heated at 70-75° C. under TLC and HPLC monitoring. After completion of the reaction, THF was evaporated and the reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. After purification, the title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Workup

customwas evaporated
customthe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customAfter purification
customthe title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Sources & evidence

ORD record: ord-51e2f1efc7c34241b66e8e50c59a693e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735627B2

Reaction notes

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