Triethylamine → HCID 67296679, compound

HRID 716781Notes

Reaction equation

HRID 716781 reaction equation
CCN(CC)CC.Br[C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:24])[CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:12]=[CH:13][CH:14]=1.[CH2:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:26]=[CH2:27].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:18]([CH:17]([CH2:21][CH2:22][CH3:23])[C:16]([NH:15][C:11]1[CH:10]=[C:9](/[CH:27]=[CH:26]/[CH2:25][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:14]=[CH:13][CH:12]=1)=[O:24])[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 11841479HCID 11841479, compound

Product 1

HCID 67296679HCID 67296679, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Et3N (1.2 mL) was added to a solution of N-(3-bromophenyl)-2-propylpentanamide (0.6 g, 2.01 mmol), tert-butyl allylcarbamate (1.026 g, 6.55 mmol) and P(o-tol)3 (0.06 g, 0.201 mmol) in DMF (10 mL). The reaction mixture was degassed for 30 min and then added Pd(OAc)2 (0.09 g, 0.409 mmol) was added. The reaction mixture was again degassed for 15 min and then refluxed at 90° C. for 8 h. The reaction mixture was diluted with EtOAc, washed with H2O, brine. The organic layer was concentrated under reduced pressure. Purification by column chromatography(100-200 mesh silica, elution 10% to 15% EtOAc in hexane) gave (E)-tert-butyl 3-(3-(2-propylpentanamido)phenyl)allylcarbamate as a yellow oil. Yield (0.7 g, 37%). 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.43 (t, J=7.6 Hz, 1H), 7.24 (s, 1H), 7.08 (dd, J=1.2, 7.2 Hz, 2H), 6.48 (d, J=16.0 Hz, 1H), 6.26-6.16 (m, 1H), 4.67 (bs, 1H), 3.89 (bs, 2H), 2.17-2.04 (m, 1H), 1.73-1.64 (m, 4H), 1.48 (s, 9H), 1.45-1.14 (m, 4H), 0.91 (t, J=7.2 Hz, 6H).

Workup

  1. customThe reaction mixture was degassed for 30 min
  2. customThe reaction mixture was again degassed for 15 min
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed with H2O, brine
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customPurification
  7. washby column chromatography(100-200 mesh silica, elution 10% to 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-9d87e490649c447daf20e9d45934d057
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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