Phenethylamine → HCID 18597314, compound

HRID 1980829Notes

Reaction equation

HRID 1980829 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:7])=[O:5])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.CN1CCOCC1>CN(C=O)C>[CH2:39]([NH:47][C:14](=[O:16])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][C@@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:7])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18597313HCID 18597313, compound

Product 1

HCID 18597314HCID 18597314, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N[1-(R)-Ethoxycarbonylethyl]-L-leucine (1.39 g, 6 mM), N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.16 g, 6 mM), 1-hydroxybenzotriazole (0.93 g, 6 mM) and phenethylamine (0.7 g, 6 mM) were dissolved in DMF (50 ml) at -6°. N-Methyl-morpholine (0.62 g, 6.2 mM) was added and the reaction mixture allowed to warm to room temperature. After 12 h the solvent was removed in vacuo. The residue in EtOAc (150 ml) was washed with H2O (2×100 ml), dried and evaporated in vacuo to yield an oil which was purified by chromatography on SiO2 in EtOAc to give N[1-(R)-ethoxycarbonylethyl]-L-leucine N-phenethylamide as an oil (1.84 g). For analysis, a portion of this material was dissolved in MeOH, treated with anhydrous HCl in Et2O and evaporated in vacuo to yield the corresponding hydrochloride as a foam; (Found: C,60.28; H,8.54; N,7.35; C19H30N2O3.HCl.0.4H2O (requires C,60.35; H,8.48; N,7.41%); [α]D20 =+9.4° (c=0.2, MeOH); νmax (Nujol) 3400 (br), 3100 (br), 2510 (br), 2400 (br), 1740, 1670 and 1550 cm-1 ; δ(CDCl3) 0.92 and 0.95 (6H, each d, each J=7 Hz, (CH3)2CH), 1.27 (3H, t, J=6.5 Hz, CH3CH2), 1.28 (3H,d,J=7 Hz, CH3CH), 1.3-1.7 (3H,m,CH2CH), 2.85 (2H,t,J=6 Hz,CH2CH2C6H5), 3.21 (1H,dd,J=10 Hz and 4 Hz, α--CH), 3.27 (3H,q,J=6.5 Hz, CH3CH), 3.54 (2H,q,J=7 Hz, NHCH2CH2), 4.16 and 4.18 (2H, each q, each J=6.5 Hz, OCH2CH3) and 7.25 (6H,m,C6H5 and NHCO).

Workup

  1. customAfter 12 h the solvent was removed in vacuo
  2. washThe residue in EtOAc (150 ml) was washed with H2O (2×100 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customto yield an oil which
  6. customwas purified by chromatography on SiO2 in EtOAc

Sources & evidence

ORD record
ord-54399378b7264fd8be63141906c03773
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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