Phenethylamine → HCID 15612343, compound

HRID 1781192Notes

Reaction equation

HRID 1781192 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]([CH3:33])([C:30]([OH:32])=O)[CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.C1(N=C=NC2CCCCC2)CCCCC1.[CH:61]1[CH:66]=[CH:65][C:64]([CH2:67][CH2:68][NH2:69])=[CH:63][CH:62]=1>C(OCC)(=O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]([CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)([CH3:33])[C:30](=[O:32])[NH:69][CH2:68][CH2:67][C:64]3[CH:65]=[CH:66][CH:61]=[CH:62][CH:63]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 19047805Fmoc-alpha-methyl-DL-tryptophan

Product 1

HCID 15612343HCID 15612343, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of N-[(9H-fluoren-9-ylmethyloxy)-carbonyl]-α-methyl-DL-tryptophan (8.80 g, 20 mmol) in dry ethyl acetate (350 mL) was added pentafluorophenol (3.68 g, 20 mmol) and stirred for 10 minutes. The reaction mixture was cooled to 0° C. and a solution of dicyclohexylcarbodiimide (20 mmol) in ethyl acetate (25 mL) was added dropwise. This solution was stirred for one hour at 0° C. then at room temperature for four hours before leaving it at 4° C. overnight. The mixture was filtered and the precipitate washed with cold ethyl acetate (30 mL) and a solution of 2-phenethylamine (2.66 g, 22 mmol) in ethyl acetate (30 mL) was added dropwise to the combined filtrates. The mixture was left to stir for 48 hours at room temperature. The reaction mixture was filtered and the residue washed with cold ethyl acetate (2×30 mL) to give the title compound (3.73 g, 75%). The filtrates were combined and the solvent removed in vacuo and taken up again in ethyl acetate (5 mL) to give a second crop of 1.67 g (15%), a total of 90% yield as a white solid, mp 179°-181° C. (EtOAc); IR (film) 1708, 1652 cm-1 ; NMR (DMSO d6) δ1.30 (3H, s), 2.64 (2H, t, J 7.2 Hz), 3.2-3.3 (4H, m), 4.19 (1H, t, J 6.7 Hz), 4.25-4.40 (2H, m), 6.9-7.9 (20 H, m), 10.8 (1H, s).

Workup

  1. stirringThis solution was stirred for one hour at 0° C.
  2. customat room temperature for four hours before leaving it at 4° C. overnight
  3. filtrationThe mixture was filtered
  4. washthe precipitate washed with cold ethyl acetate (30 mL)
  5. waitThe mixture was left
  6. stirringto stir for 48 hours at room temperature
  7. filtrationThe reaction mixture was filtered
  8. washthe residue washed with cold ethyl acetate (2×30 mL)

Sources & evidence

ORD record
ord-a69ca275761d4c46a111a322f087a9f1
Source dataset
uspto-grants-1997_05
Patent number
US05631281

Reaction notes

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