Triethylamine → di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{(E)-3-[4-(3-hydroxypropyl)phenyl]prop-2-en-1-yl}-L-glutamate

HRID 591288Notes

Reaction equation

[CH2:1]([C@H:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][C@@H:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:2]=[CH2:3].I[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][OH:39])=[CH:32][CH:31]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:10][C:8]([NH:7][C@H:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][C@H:4]([CH2:1]/[CH:2]=[CH:3]/[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][OH:39])=[CH:32][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of di-tert-butyl (4S)-4-allyl-N-(tert-butoxycarbonyl)-L-glutamate (940 mg, 2.53 mmol) in 5 mL acetonitrile under an argon atmosphere was added 3-(4-iodophenyl)propan-1-ol (740 mg, 2.82 mmol), triethylamine (394 μl, 2.82 mmol), and palladium(II) acetate (106 mg, 0.47 mmol). The mixture was stirred in a pressure tube at 80° C. for 2 h. After cooling to room temperature, the solvent was removed under reduced pressure and the crude material was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure
customthe crude material was purified on silica gel using a hexane/ethyl acetate gradient
concentrationconcentrated

Sources & evidence

ORD record: ord-44fe778f3dae4b3cb19d67273d40fc0d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238631B2

Reaction notes

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