L-Phenylalanine → HCID 11808095, compound

HRID 2250862Notes

Reaction equation

HRID 2250862 reaction equation
N[C@H](C(O)=O)CC1C=CC=CC=1.[NH:13]([N:25]=[N+:26]=[N-:27])[C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:53]([NH2:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C>[NH:13]([N:25]=[N+:26]=[N-:27])[C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[N:13]([C@@H:14]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]([NH:60][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:24])=[N+:25]=[N-:26]

Participants

8

Reactant 5

HCID 6140L-PhenylalanineHCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 66669689HCID 66669689, compound

Product 2

HCID 11808095HCID 11808095, compoundHCID 66669689HCID 66669689, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N3(L)PheOH (1SL) was synthesized from L-phenylalanine essentially by the procedure of Lundquist and Pelletier.17 N3(L)PheOH (1.08 g, 5.7 mmol) was dissolved in anhydrous DMF (40 mL). HOBt (0.87 g, 5.7 mmol) was then added, followed by DCC (1.17 g, 5.7 mmol). Once precipitate was observed in the reaction, benzyl amine (0.62 mL, 5.7 mmol) was added. The reaction was allowed to stir under Ar(g) for 3 h. The resulting precipitate (DCU) was removed by filtration, and the filtrate was concentrated under reduced pressure to give a yellow oil. This oil was purified by flash chromatography (silica gel, 35% v/v/ethyl acetate in hexanes). N3(L)Penh (48-L) was isolated as an off-white solid in 90% yield. The procedure was repeated with D-phenylalanine to give N3(D)Penh products (D and L enantiomers) are identical. N3(L)Penh (48-L) 1H NMR (500 MHz, CDCl3 δ 7.31-7.12 (m, 8H), 7.11 (m, 2H), 6.55 (bus, 1H), 4.38 (m, 2H), 4.22 (did, J=7.8, 4.6 Hz, 1H), 3.34 (did, J=14.0, 4.5 Hz, 1H), 3.07 (did, J=14.1, 7.5 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 168.30, 137.35, 135.96, 129.51, 128.61, 128.66, 128.61, 128.55, 127.70, 127.68, 127.66, 127.57, 127.16, 65.40, 43.41, 38.41 ppm; MS (ESI) m/z 303.1235 (MNa+[C16H16N4ONa]=303.1222).

Workup

  1. additionwas added
  2. customThe resulting precipitate (DCU) was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a yellow oil
  5. customThis oil was purified by flash chromatography (silica gel, 35% v/v/ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7b949382db4d42278daa21e7ccb53633
Source dataset
uspto-grants-2008_01
Patent number
US07317129B2

Reaction notes

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