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

HRID 591296Notes

Reaction equation

HRID 591296 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].[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40](I)=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40](/[CH:3]=[CH:2]/[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:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5196711-(Benzyloxy)-4-iodobenzeneHCID 58185190Di-tert-butyl (2S,4S)-2-Allyl-4-(Boc-amino)pentanedioate

Product 1

HCID 117812694Di-tert-butyl (4S)-4-{(E)-3-[4-(benzyloxy)phenyl]prop-2-en-1-yl}-N-(tert-butoxycarbonyl)-L-glutamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent3×

Conditions

Temperature
80 °C

Procedure

To a stirred solution of di-tert-butyl (4S)-4-allyl-N-(tert-butoxycarbonyl)-L-glutamate (345 mg, 0.86 mmol) in acetonitrile (5 ml) at room temperature was slowly added 1-(benzyloxy)-4-iodobenzene (ABCR GmbH & CO. KG) (321 mg, 1.04 mmol) in 3 ml acetonitrile, triethylamine (144 μl, 1.04 mmol) in 3 ml acetonitrile, and palladium(II) acetate (Aldrich) (39 mg, 0.17 mmol). The mixture was heated in a pressure tube at 80° C. for 2 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated in vacuo. The crude material was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. customat room temperature
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude material was chromatographed on silica gel using a hexane/ethyl acetate gradient
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-486ea89b85684bb9b01ef12c9bf86076
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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