Putrescine → L-Phenylalanine

HRID 2229868Notes

Reaction equation

HRID 2229868 reaction equation
C[N:2](C)[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(CC)CC.NCCCCN>CC#N>[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1045PutrescineHCID 8471TriethylamineHCID 1183028917469-89-5

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-dimethylphenylalanine (15) (1.19 g, 6.2 mmol), Et3N (1.29 ml, 9.3 mmol), and 1,4-diamino butane (303 μl, 3.0 mmol) were dissolved in CH3CN (50 mL). O-benzotriole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU) was added, and the reaction mixture was stirred at room temperature for 30 minutes, and then concentrated under reduced pressure. The mixture was vacuum filtered (EtOAc), further concentrated under reduced pressure, and subjected to flash chromatography (EtOAc, then 10% Et3N in EtOAc) to afford 1.06 g (80%, non-optimized) of (16a) as white crystals. [α]25−105.7 (c=0.19, CHCl3); FTIR (neat) 1649, 1455, 1384, 748, 700 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.19-7.16 (m, 8H), 6.89 (t, J=5.7 Hz, 211), 6.40 (s, 1H), 5.90 (s, 1H), 3.13-3.04 (m, 6H), 3.12 (dd, J=12.7, 5.3 Hz, 2H), 2.79 (dd, J=13.4, 5.1 Hz, 2H), 2.23 (s, 12H), 1.24 (s, 4H); 13C NMR (100 MHz, CDCl3) δ 171.68, 129.44, 128.88, 127.91, 125.69, 70.61, 41.91, 38.25, 32.84, 26.52; HRMS calculated for C26H39N4O2 (M+H)+ required 439.3073, found 439.3074.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered (EtOAc)
  3. concentrationfurther concentrated under reduced pressure

Sources & evidence

ORD record
ord-3fb464c65bef4916b47bb35320d4f3da
Source dataset
uspto-grants-2002_07
Patent number
US06420586B1

Reaction notes

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