Triethylamine → HCID 54374113, compound

HRID 1736616Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=O)=O.C(N(CC)CC)C.[C:33]([O:37][CH2:38]C)(=[O:36])[CH:34]=[CH2:35].C(OCC)(=O)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:35]=[CH:34][C:33]([O:37][CH3:38])=[O:36])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3.27 g (8.54 mmol) of 2-[3-(tert-butoxycarbonylamino)propyl]phenyl trifluoromethanesulfonate, 3.62 ml (26 mmol) of triethylamine 1.15 ml (12.8 mmol) of ethyl acrylate and 0.2 g (0.3 mmol) of his (triphenylphosphine) palladium (II) chloride was heated at 110° C. in a sealed heavy-walled Pyrex, Teflon screw-capped flask for 16 hours. Ethyl acetate (100 ml) and water (100 ml) were added to the reaction mixture after it was cooled to 25° C. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated. The residue was chromotographed on a silica gel column, eluting with a 5 to 25% gradient of ethyl acetate in hexane to afford 1.85 g (68%) of the product as an oil.

Workup

extractionThe aqueous phase was extracted with ethyl acetate
washThe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
washeluting with a 5 to 25% gradient of ethyl acetate in hexane

Sources & evidence

ORD record: ord-db2110161dcc4329ad38bf6bd3544a30
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541286

Reaction notes

Loading…