Acetic Acid → HCID 20662286, compound

HRID 1067085Notes

Reaction equation

HRID 1067085 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:25])[C@H:12]([CH2:14][CH2:15][CH2:16][NH:17]C(OC(C)(C)C)=O)[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[C:30]1([CH2:36][CH:37]=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([BH3-])#N.[Na+]>CO>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:25])[C@H:12]([CH2:14][CH2:15][CH2:16][NH2:17])[NH:13][CH2:37][CH2:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131722654HCID 131722654, compound

Product 1

HCID 20662286HCID 20662286, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A cold solution (0° C.) of the above amine (3 g, 8.6 mmol), in methanol (20 ml), was treated sequentially with acetic acid (345 μl, 6 mmol) and phenylacetaldehyde (1.2 ml, 10 mmol). Then a solution of sodium cyanoborohydride (2.7 g, 43 mmol) in methanol (10 ml) was added to the mixture slowly. The reaction was stirred for additional 30 minutes and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed with aqueous sodium bicarbonate, and purified by chromatography (silica gel, hexane/ethyl acetate) to afford Nα-(phenethyl)ornithine 3-phenylpropylamide (2.64 g): 1H NMR (400 MHz, CD3OD) δ1.4 (s, 9H), 1.45-1.8 (m, 6H), 2.6 (t, J=6.4 Hz, 2H), 2.65-2.8 (m, 4H), 3.02-3.2 (m, 5H), and 7.1-7.3 (m, 10H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate
  4. custompurified by chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ac795a449ee6463dbef1930883402b85
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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