Triethylamine → Amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide

HRID 1720648Notes

Reaction equation

HRID 1720648 reaction equation
[NH2:1][C@H](C(O)=O)CCCC.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.Cl.[CH2:35]([NH:39][C:40](=[O:53])[CH:41]([CH2:51][CH3:52])[CH2:42][C@H:43]([OH:50])[C@@H:44](N)[CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([NH:39][C:40](=[O:53])[C:41]([NH2:1])([CH2:51][CH3:52])[CH2:42][CH:43]([OH:50])[CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 21236CaprineHCID 199401P,P-Diphenylphosphinic azideHCID 14582181(2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide monohydrochloride

Product 1

HCID 54242229Amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

20.7 mg of L-N-[(2R or S)-5-ethylthio-2-(1-naphthylmethyl)pentanoyl]norleucine was dissolved in 0.5 ml of dry DMF. Then, 17.4 μl of triethylamine, 12.9 μl of DPPA and 20 mg of (2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide monohydrochloride was added thereto under stirring at -15° C. The mixture was stirred at the same temperature for one hour and then at 5° C. overnight. The reaction solution was diluted with 20 ml of ethyl acetate, washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain 16.9 mg of (2RS,4S,5S)-5-{L-N-[(2R or S)-5-ethylthio-2-(1-naphthylmethyl)pentanoyl]norleucyl}-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide as colorless solid.

Workup

  1. stirringThe mixture was stirred at the same temperature for one hour
  2. customat 5° C.
  3. customovernight
  4. washwashed with water and with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-8f77fe0b30724cd0a0061f4b04abc798
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

Loading…