Octylamine → Boc-l-phenylalanine octyl amide

HRID 1991438Notes

Reaction equation

HRID 1991438 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[NH:17]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:18]([C:26](ON1C(=O)CCC1=O)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:1]([NH:9][C:26](=[O:27])[C@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:17][C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8143OctylamineHCID 8471TriethylamineHCID 107447tert-butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamate

Product 1

HCID 68538003Boc-l-phenylalanine octyl amideYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-octylamine (0.9 g, 6.9 mmol) and triethylamine (0.7 g, 6.9 mmol) in ethyl acetate (80 ml) was added a solution of BOC-Phe-OSu (2.5 g, 6.9 mmol) in ethyl acetate (50 ml). The mixture was stirred at room temperature for 20 hours. The organic layer was washed with water, 10% sodium carbonate, water and brine and denied on MgSO4. Evaporation of the solvent in vacuo yielded MdL080 as a white powder (2.5 g, 6.6 mmol, 96%). 1H NMR (CDCl3): δ=7.26-7.14 (m, 5H), 5.59 (bp 1H), 5.02 (bp, 1H), 4.20 (m, 1H), 3.07 (m, 4H), 1.57-1.17 (m, 21H), 0.82 (t, 3H, 3J=6.8 Hz); 13C NMR (CDCl3): δ=170.98, 136.68, 129.19, 128.60, 126.76, 65.88, 39.34, 88.71, 31.66, 29.21, 29.07, 28.16, 26.64, 22.52, 13.97.

Workup

  1. washThe organic layer was washed with water, 10% sodium carbonate, water and brine
  2. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-5b5dfe79c41a4648bed1604e77acb846
Source dataset
uspto-grants-2010_01
Patent number
US07645805B2

Reaction notes

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